JP2022113680A - Molecule having one hydrophobic group and two identical hydrophilic ion groups, and composition thereof - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a compound of a novel class.

SOLUTION: A novel compound to be disclosed has a hydrophobic group and two identical hydrophilic ion groups. The two hydrophilic groups of the disclosed compound contain cationic or anionic charged groups or terminate by themselves. A method for synthesizing the novel compound to be disclosed is also described. The novel compound disclosed in the description can be used as a surfactant in an article, a product, or a composition, or for several other purposes. A corrosion control composition containing a dicationic or a dianionic compound, and a method of application thereof in the corrosion control composition for reducing corrosion of a surface in an aqueous system are also disclosed in the description. It has been found that the method or the composition to be disclosed is more effective than a method or a composition containing a single quaternary compound generally used for alleviating corrosion of a metal surface in the aqueous system.

SELECTED DRAWING: Figure 1

COPYRIGHT: (C)2022,JPO&INPIT

Description

関連出願の相互参照 本出願は、“ＭＯＬＥＣＵＬＥＳ ＨＡＶＩＮＧ ｏｎｅ ｈｙｄｒｏｐｈｏｂｉｃ ＡＮＤ ＴＷＯ ＩＤＥＮＴＩＣＡＬ ｈｙｄｒｏｐｈｉｌｉｃ ｇｒｏｕｐｓ ＡＮＤ Ｃｏｍｐｏｓｉｔｉｏｎｓ ＴＨＥＲＥＯＦ ａｎｄ Ｍｅｔｈｏｄｓ ｏｆ ＰｒｅｐａｒＡＴＩＯＮ ＴＨＥＲＥＯＦ ａｎｄ Ｍｅｔｈｏｄｓ ｏｆ ＰｒｅｐａｒＡＴＩＯＮ ＴＨＥＲＥＯＦ”と題する、２０１７年８月３０日に出願された、米国仮出願No. 62/552,108 claims priority to and is related thereto. The entire contents of this patent application, including, but not limited to, the specification, claims, and abstract, and any figures, tables, or drawings thereof, are expressly incorporated herein by reference.

The present disclosure relates generally to the field of surfactant compounds, methods of making them, methods of using them as corrosion control agents, and corrosion control compositions. Specifically, the present disclosure relates to a new class of compounds containing two identical hydrophilic cationic or anionic groups and one hydrophobic group. The disclosed compounds share some structural features with conventional surfactants or gemini surfactants, but are structurally distinguishable from existing surfactants. The disclosed compounds are useful alone or together with other conventional surfactants or gemini surfactants as surfactants in a variety of applications. The compounds disclosed herein have also been found to be effective corrosion inhibitors.

Surfactant compounds usually contain a hydrophilic group and a hydrophobic group. Due to their unique structure, surfactants have various uses in different fields. As the understanding of the structure of surfactant compounds and their relationship to their function and mode of operation increases, the need for surfactant compounds with new or improved properties, such as surface tension properties, increases.

Although surfactant structures are diverse and numerous, existing surfactants can be divided into two broad categories, the conventional surfactant category and the gemini surfactant category.

Conventional surfactants usually have a hydrophobic group and a hydrophilic group. Depending on the characteristics of the hydrophilic group, conventional surfactants can be one of nonionic, anionic, cationic, amphoteric, or zwitterionic surfactants.

Gemini surfactants, on the other hand, have two hydrophobic groups and two hydrophilic groups. Gemini surfactants can be further divided into similar subcategories based on the characteristics of the hydrophobic group(s), in a manner analogous to that used to classify conventional surfactants.

It is therefore an aim to develop novel surfactant compounds that have properties distinguishable from conventional surfactants and/or gemini surfactants. In both conventional surfactants and gemini surfactants, the ratio of hydrophilic to hydrophobic groups is 1:1, whereas the disclosed compounds have a ratio of hydrophilic to hydrophobic groups of 2:1. This difference in the ratio of hydrophilic to hydrophobic groups is useful not only as surfactants, but also as antimicrobial agents, fungicides, fabric softeners, antistatic agents, corrosion inhibitors, blowing agents, flotation agents, dispersants, Surfactant-assisted enhanced oil recovery (EOR) cleaners and the like also provide unique uses for the disclosed compounds.

A further object of this disclosure is to develop methods for efficiently and effectively making novel compounds.

A further object of this disclosure is to use the novel compounds in articles, products, and/or compositions.

Additionally, quaternary ammonium compounds comprise an important subcategory of surfactants as they contain unique properties. A major difference between quaternary ammonium compounds and other surfactants is their unique structure. Quaternary ammonium compounds consist mainly of two parts, a hydrophobic group, such as a long alkyl group, and a quaternary ammonium base. The unique positive charge of ammonium, for example, plays an important role, electrostatic interactions between surfactants and surfaces.

Industrial water systems use process water to serve many different purposes and can be prone to microbial contamination and fouling. Metal surfaces in any water system are susceptible to corrosion, in part due to microbial contamination and fouling.

Corrosion inhibitors are often added to water systems to protect their metallic surface infrastructure, such as carbon steel pipelines, from corrosion. However, the quaternary ammonium compounds used for such purposes, often of the bis-quaternary species or species quaternized with benzyl chloride, are known to be highly hazardous. Additionally, government regulations exist to release any water containing a single quaternary compound into the environment.

Therefore, there is a continuing need for different or alternative quaternary ammonium compounds that are better and safer corrosion control agents.

It is therefore also an object of the present disclosure to develop new corrosion control agents with improved corrosion control properties.

A further object of the present disclosure is to develop methods and corrosion control compositions for making corrosion in water systems more efficient and effective.

These and other objects, advantages, and features of the present disclosure will become apparent from the following specification, along with the claims set forth herein.

Disclosed herein are novel compounds, including surfactant compounds, compositions comprising the disclosed compounds, and methods of making the disclosed compounds. More specifically, disclosed herein are compounds containing two identical hydrophilic groups and a single hydrophobic group. In the disclosed compounds, each hydrophilic group contains or terminates in a quaternary amine or negatively charged species, and the hydrophobic groups contain long hydrophobic chains. Because the ratio of hydrophilic to hydrophobic groups in closed compounds is 2:1, whereas in conventional surfactants or gemini surfactants the ratio is 1:1, the disclosed compounds are superior to conventional Unlike surfactants or gemini surfactants. This difference in structure is not only used as a surfactant, but also as an antibacterial disinfectant, fabric softener, antistatic agent, corrosion inhibitor, blowing agent, flotation collector, dispersant, surfactant-assisted petroleum Other purposes such as enhanced recovery (EOR) detergents also provide unique uses for the disclosed compounds.

式中、
Ｘは、ＮＨまたはＯであり、
Ｒ^１１は、Ｒ^１またはＲ^１－Ｚ－（ＣＨ_２）_ｍ－であり、
Ｒ^１は、非置換もしくは置換の直鎖もしくは分岐鎖Ｃ_１～Ｃ_３０アルキル、環状アルキル、アルケニル、またはアルキニル基であり、
Ｚは、ＮＨまたはＯであり、
Ｒ^２は、Ｈ、ＣＨ_３、または非置換の直鎖もしくは分岐鎖Ｃ_１～Ｃ_１０アルキル、アルケニル、もしくはアルキニル基であり、
ｍは、１～４の整数であり、
Ｒ^３は、存在しないか、または非置換の直鎖Ｃ_{１～Ｃ３０}アルキレン基であり、
Ｙは、－ＮＲ^４Ｒ^５Ｒ^６（＋）またはその塩であり、
Ｒ^４、Ｒ^５、およびＲ^６は独立して、Ｃ_１～Ｃ_１０アルキル基である。 In one aspect, there is provided a compound I according to formula I,

During the ceremony,
X is NH or O;
R ¹¹ is R ¹ or R ¹ -Z-(CH ₂ ) _m -;
R ¹ is an unsubstituted or substituted straight or branched chain C ₁ -C ₃₀ alkyl, cyclic alkyl, alkenyl, or alkynyl group;
Z is NH or O;
R ² is H, CH ₃ , or an unsubstituted straight or branched chain C ₁ -C ₁₀ alkyl, alkenyl, or alkynyl group;
m is an integer from 1 to 4,
R ³ is absent or an unsubstituted linear C1 _-C30 alkylene group;
Y is -NR ⁴ R ⁵ R ^{6 (+)} or a salt thereof;
R ⁴ , R ⁵ and R ⁶ are independently C ₁ -C ₁₀ alkyl groups.

であり、Ｘは、ＮＨまたはＯであり、
Ｒ^１１は、Ｒ^１またはＲ^１－Ｚ－（ＣＨ_２）_ｍ－であり、
Ｒ^１は、非置換もしくは置換の直鎖もしくは分岐鎖Ｃ_１～Ｃ_３０アルキル、環状アルキル、アルケニル、またはアルキニル基であり、
Ｚは、ＮＨまたはＯであり、
Ｒ^２は、Ｈ、ＣＨ_３、または非置換の直鎖もしくは分岐鎖Ｃ_２～Ｃ_１０アルキル、アルケニル、もしくはアルキニル基であり、
ｍは、１～４の整数であり、
Ｒ^３は、存在しないか、または非置換の直鎖Ｃ_{１～Ｃ３０}アルキレン基であり、
Ｙは、－ＮＲ^４Ｒ^５Ｒ^６（＋）またはその塩であり、
Ｒ^４、Ｒ^５、およびＲ^６は独立して、Ｃ_１～Ｃ_１０アルキル基である。 In another aspect, disclosed herein are methods for synthesizing the disclosed compounds. The method comprises contacting a primary amine with an activated olefin containing at least one cationic group to produce a compound disclosed herein, wherein the primary amine is R ¹¹ —NH ₂ and R ¹¹ is R ¹ or R ¹ -Z-(CH ₂ ) _m - and the activated olefin is

and X is NH or O;
R ¹¹ is R ¹ or R ¹ -Z-(CH ₂ ) _m -;
R ¹ is an unsubstituted or substituted straight or branched chain C ₁ -C ₃₀ alkyl, cyclic alkyl, alkenyl, or alkynyl group;
Z is NH or O;
R ² is H, CH ₃ , or an unsubstituted straight or branched chain C ₂ -C ₁₀ alkyl, alkenyl, or alkynyl group;
m is an integer from 1 to 4,
R ³ is absent or an unsubstituted linear C1 _-C30 alkylene group;
Y is -NR ⁴ R ⁵ R ^{6 (+)} or a salt thereof;
R ⁴ , R ⁵ and R ⁶ are independently C ₁ -C ₁₀ alkyl groups.

In yet another aspect, provided herein are articles, manufactures, or compositions comprising one or more compounds disclosed herein.

In yet another aspect, provided herein are compositions comprising one or more compounds disclosed herein.

Also disclosed herein are methods and compositions for corrosion control of metal surfaces in aqueous systems. Specifically, the disclosed methods and compositions for corrosion control of aqueous systems are derived from one The above water-soluble dicationic or dianionic compounds are used.

Exemplary dicationic or dianionic compounds disclosed herein have superior performance over conventional single quaternary ammonium compounds used to mitigate corrosion of metal surfaces in aqueous systems. Exemplary dicationic or dianionic compounds disclosed herein also exhibit improved performance when used as fouling control agents in aqueous systems. Thus, the disclosed corrosion control compositions or methods not only inhibit surface corrosion, but also inhibit microbial/biofilm growth, reducing the chemical use, cost, and operational complexity of manipulating water systems. has the advantage of providing an overall reduction in

式中、Ｘは、ＮＨまたはＯであり、Ｒ^１１は、Ｒ１またはＲ^１－Ｚ－（ＣＨ_２）_ｍ－であり、Ｒ^１は、非置換もしくは置換の直鎖もしくは分岐鎖Ｃ_１～Ｃ_３０アルキル、環状アルキル、アルケニル、またはアルキニル基であり、Ｚは、ＮＨまたはＯであり、Ｒ^２は、Ｈ、ＣＨ_３、または非置換の直鎖または分岐鎖Ｃ_２～Ｃ_１０アルキル、アルケニル、またはアルキニル基であり、ｍは、１～４の整数であり、Ｒ^３は、存在しないか、または非置換の直鎖Ｃ_１～Ｃ_３０アルキレン基であり、Ｙは、－ＮＲ^４Ｒ^５Ｒ^６（＋）であり、Ｙ’は、－ＣＯＯＨ、－ＳＯ_３Ｈ、－ＰＯ_３Ｈ、－ＯＳＯ_３Ｈ、－ＯＰＯ_３Ｈ、またはそれらの塩であり、Ｒ^４、Ｒ^５、およびＲ^６は独立して、Ｃ_１～Ｃ_１０アルキル基であり、Ｒ^２’は、Ｈ、ＣＨ_３、または非置換もしくは置換の直鎖もしくは分岐鎖Ｃ_１～Ｃ_１０アルキル、アルケニル、アルキニル基、－ＣＯＯＨ、－ＣＨ_２ＣＯＯＨ、Ｙ’、または－（ＣＨ_２）_ｍ－Ｙ’であり、腐食制御組成物は、水系中の表面上の腐食を緩和する。 In one aspect, disclosed herein is a method for inhibiting corrosion on a surface in an aqueous system, the method comprising providing a corrosion control composition or a use solution of the corrosion control composition into an aqueous system to treat treated forming a water-based system or providing on a surface of the water-based system, the corrosion control composition comprising one or more compounds according to one of Formula I, Formula II, and Formula III; an additional corrosion control composition agent of

wherein X is NH or O, R ¹¹ is R1 or R ¹ -Z-(CH ₂ ) _m -, and R ¹ is unsubstituted or substituted straight or branched chain C ₁ -C ₃₀ alkyl, cyclic alkyl, alkenyl, or alkynyl group, Z is NH or O, R ² is H, CH ₃ , or unsubstituted straight or branched chain C ₂ -C ₁₀ alkyl, alkenyl, or an alkynyl group, m is an integer from 1 to 4, R ³ is absent or an unsubstituted linear C ₁ -C ₃₀ alkylene group, and Y is —NR ⁴ R ⁵ R ⁶⁽⁺⁾ , Y′ is —COOH, —SO ₃ H, —PO ₃ H, —OSO ₃ H, —OPO ₃ H, or salts thereof, and R ⁴ , R ⁵ and R ⁶ is independently a C ₁ -C ₁₀ alkyl group and R ^2′ is H, CH ₃ , or an unsubstituted or substituted straight or branched chain C ₁ -C ₁₀ alkyl, alkenyl, alkynyl group, —COOH , —CH ₂ COOH, Y′, or —(CH ₂ ) _m —Y′, and the corrosion control composition mitigates corrosion on surfaces in aqueous systems.

式中、Ｘは、ＮＨまたはＯであり、Ｒ^１１は、Ｒ^１またはＲ^１－Ｚ－（ＣＨ_２）_ｍ－であり、Ｒ^１は、非置換もしくは置換の直鎖もしくは分岐鎖Ｃ_１～Ｃ_３０アルキル、環状アルキル、アルケニル、またはアルキニル基であり、Ｚは、ＮＨまたはＯであり、Ｒ^２は、Ｈ、ＣＨ_３、または非置換の直鎖または分岐鎖Ｃ_２～Ｃ_１０アルキル、アルケニル、またはアルキニル基であり、ｍは、１～４の整数であり、Ｒ^３は、存在しないか、または非置換の直鎖Ｃ_１～Ｃ_３０アルキレン基であり、Ｙは、－ＮＲ^４Ｒ^５Ｒ^６（＋）であり、Ｙ’は、－ＣＯＯＨ、－ＳＯ_３Ｈ、－ＰＯ_３Ｈ、－ＯＳＯ_３Ｈ、－ＯＰＯ_３Ｈ、またはそれらの塩であり、Ｒ^４、Ｒ^５、およびＲ^６は独立して、Ｃ_１～Ｃ_１０アルキル基であり、Ｒ^２’は、Ｈ、ＣＨ_３、または非置換もしくは置換の直鎖もしくは分岐鎖Ｃ_１～Ｃ_１０アルキル、アルケニル、アルキニル基、－ＣＯＯＨ、－ＣＨ_２ＣＯＯＨ、Ｙ’、または－（ＣＨ_２）_ｍ－Ｙ’であり、腐食制御組成物は、水系中の表面上の腐食を緩和する。 In another aspect, corrosion control compositions are disclosed herein comprising one or more compounds according to one of Formula I, Formula II, and Formula III and one or more additional and a corrosion control composition of

wherein X is NH or O, R ¹¹ is R ¹ or R ¹ -Z-(CH ₂ ) _m -, and R ¹ is unsubstituted or substituted straight or branched chain C ₁ to C ₃₀ alkyl, cyclic alkyl, alkenyl, or alkynyl group, Z is NH or O, R ² is H, CH ₃ , or unsubstituted straight or branched chain C ₂ -C ₁₀ alkyl, alkenyl , or an alkynyl group, m is an integer from 1 to 4, R ³ is absent or an unsubstituted linear C ₁ -C ₃₀ alkylene group, Y is —NR ⁴ R ⁵ R ⁶⁽⁺⁾ , Y′ is —COOH, —SO ₃ H, —PO ₃ H, —OSO ₃ H, —OPO ₃ H, or a salt thereof, and R ⁴ , R ⁵ and R ⁶ is independently a C ₁ -C ₁₀ alkyl group and R ^2′ is H, CH ₃ , or an unsubstituted or substituted straight or branched chain C ₁ -C ₁₀ alkyl, alkenyl, alkynyl group, — COOH, —CH ₂ COOH, Y′, or —(CH ₂ ) _m —Y′, the corrosion control composition moderates corrosion on surfaces in aqueous systems.

The above summary is exemplary only and is not intended to be limiting in any way. In addition to the exemplary aspects, embodiments, and features described above, further aspects, embodiments, and features of the present technology can be found in the following drawings and detailed description, which illustrate and describe exemplary embodiments of the present technology. will become apparent to those skilled in the art from. Accordingly, the drawings and detailed description are to be regarded as illustrative in nature and not restrictive in any way.

A representation of an exemplary compound of the present disclosure (1C) is shown along with a comparative representation of a conventional surfactant (1A) and a gemini surfactant (1B). A general reaction scheme between primary amines (Michael donors) and activated olefins containing cationic groups (Michael acceptors) is shown. Corrosion rates are given in mils per year (mpy) during the bubble test period (18 hours). No 2-mercaptoethanol (2ME) was added to blank samples.

Various embodiments of the invention will now be described in detail with reference to the drawings, wherein like reference numerals refer to like parts throughout the several views. Reference to various embodiments does not limit the scope of the invention. The figures shown herein are presented for exemplary explanation of the present invention and not for limitation of various embodiments according to the present invention.

Disclosed herein are novel compounds and methods of making these novel compounds or surfactant compositions. More specifically, compounds containing two identical hydrophilic groups and one hydrophobic group in the molecule and methods of synthesizing such surfactants are disclosed. For example, each hydrophilic group contains or terminates in a quaternary amine and the hydrophobic group contains a long aliphatic chain.

Embodiments of the present invention are not limited to particular compositions and methods of use, which may vary and are understood by those skilled in the art. It should further be understood that all terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting in any manner or scope. . For example, as used in this specification and the appended claims, the singular forms "a," "an," and "the" include plural referents unless the content clearly dictates otherwise. obtain. In addition, all units, prefixes and symbols may be denoted in their SI accepted form.

Numerical ranges recited within this specification are inclusive of the numbers within the defined range. Throughout this disclosure, various aspects of this invention are presented in a range format. The description in range format is merely for convenience and brevity and should not be construed as an inflexible limitation on the scope of the invention. Accordingly, the description of a range should be considered to have specifically disclosed all the possible subranges as well as individual numerical values within that range (eg, 1 to 5 is 1, 1.5, 2, 2.75, 3, 3.80, 4, and 5).

In order to make the invention easier to understand, certain terms are first defined. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which embodiments of the invention pertain. Many methods and materials similar, modified or equivalent to those described herein may be used in the practice of embodiments of the present invention without undue experimentation. Obtainable and preferred materials and methods are described herein. In describing and claiming the embodiments of the present invention, the following terminology will be used in accordance with the definitions set forth below.

The term "about," as used herein, refers to, for example, typical measurement and liquid handling procedures used in making concentrates or use-solutions in the real world, errors in these procedures, Refers to variations in quantities that may arise, such as due to differences in manufacture, source, or purity of ingredients used in carrying out the method. The term "about" also includes amounts that vary due to new equilibrium conditions for the composition resulting from a particular initial mixture. Whether or not modified by the term "about," the claims include equivalents to that amount.

As used herein, "substituted" means that one or more bonds to a hydrogen atom contained therein are replaced by a bond to a non-hydrogen or non-carbon atom: It refers to defined organic groups such as alkyl groups. Substituents also include groups in which one or more carbon atom(s) or hydrogen atom(s) is replaced by one or more bonds, including double or triple bonds to heteroatoms. be done. Thus, a substituent is substituted with one or more substituents unless otherwise specified. A substituent may be substituted with 1, 2, 3, 4, 5, or 6 substituents.

Substituted ring groups include rings and ring systems in which a bond to a hydrogen atom is replaced with a bond to a carbon atom. Thus, substituted cycloalkyl, aryl, heterocyclyl, and heteroaryl groups may also be substituted with substituted or unsubstituted alkyl, alkenyl, and alkynyl groups, as defined herein.

As used herein, the terms "alkyl" or "alkyl group" refer to saturated hydrocarbons having one or more carbon atoms and straight chain alkyl groups (e.g., methyl, ethyl, propyl, butyl, pentyl , hexyl, heptyl, octyl, nonyl, decyl, etc.), cyclic alkyl groups (or "cycloalkyl" or "alicyclic" or "carbocyclic" groups) (e.g., cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc.), branched chain alkyl groups (eg, isopropyl, tert-butyl, sec-butyl, isobutyl, etc.), and alkyl-substituted alkyl groups (eg, alkyl-substituted cycloalkyl groups and cycloalkyl-substituted alkyl groups).

Unless otherwise specified, the term "alkyl" includes both "unsubstituted alkyl" and "substituted alkyl". As used herein, the term "substituted alkyl" refers to an alkyl group having substituents replacing one or more hydrogens on one or more carbons of the hydrocarbon backbone. Such substituents include, for example, alkenyl, alkynyl, halogeno, hydroxyl, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy, aryloxy, aryloxycarbonyloxy, carboxylate, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, including aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylthiocarbonyl, alkoxyl, phosphate, phosphonate, phosphinate, cyano, amino (alkylamino, dialkylamino, arylamino, diarylamino, and alkylarylamino ), acylamino (including alkylcarbonylamino, arylcarbonylamino, carbamoyl, and ureido), imino, sulfhydryl, alkylthio, arylthio, thiocarboxylate, sulfate, alkylsulfinyl, sulfonate, sulfamoyl, sulfonamide, nitro, trifluoromethyl, Cyano, azido, heterocyclic, alkylaryl, or aromatic (including heteroaromatic) groups may be included.

In some embodiments, substituted alkyls can include heterocyclic groups. As used herein, the term “heterocyclic group” refers to a carbocyclic group in which one or more of the carbon atoms in the ring is an element other than carbon, such as nitrogen, sulfur, or oxygen. Contains similar closed ring structures. Heterocyclic groups can be saturated or unsaturated. Exemplary heterocyclic groups include, but are not limited to, aziridine, ethylene oxide (epoxide, oxirane), thiirane (episulfide), dioxirane, azetidine, oxetane, thietane, dioxetane, dithietane, dithieto, azolidine, Pyrrolidine, pyrroline, oxolane, dihydrofuran, and furan.

An alkenyl group or alkene is a straight, branched or cyclic alkyl group having from 2 to about 30 carbon atoms and further containing at least one double bond. In some embodiments, alkenyl groups have from 2 to about 30 carbon atoms, or typically from 2 to 10 carbon atoms. Alkenyl groups can be substituted or unsubstituted. In the case of double bonds in alkenyl groups, the configuration of the double bonds can be trans or cis configuration. Alkenyl groups may be substituted in the same manner as alkyl groups.

Alkenyl groups are straight chain, branched or cyclic alkyl groups having from 2 to about 30 carbon atoms and further containing at least one triple bond. In some embodiments, alkynyl groups have from 2 to about 30 carbon atoms, or typically from 2 to 10 carbon atoms. Alkynyl groups can be substituted or unsubstituted. Alkynyl groups may be substituted in the same manner as alkyl or alkenyl groups.

As used herein, the terms “alkylene,” “cycloalkylene,” “alkynilide,” and “alkenylene,” by themselves or as part of another substituent, each represent —CH ₂ CH ₂ CH ₂ refers to a divalent radical derived from an alkyl, cycloalkyl, or alkenyl group, as exemplified by -. For alkylene, cycloalkylene, alkynylene, and alkenylene groups, no orientation of the linking group is implied.

As used herein, the term “ester” refers to the —R ³⁰ COOR ³¹ group. R ³⁰ is absent, substituted or unsubstituted alkylene, cycloalkylene, alkenylene, alkynylene, arylene, aralkylene, heterocyclylalkylene, or heterocyclylene group as defined herein. R ³¹ is a substituted or unsubstituted alkyl, cycloalkyl, alkenyl, alkynyl, aryl, aralkyl, heterocyclylalkyl, or heterocyclyl group as defined herein.

As used herein, the term “amine” (or “amino”) refers to the —R ³² NR ³³ R ³⁴ group. R ³² is absent, substituted or unsubstituted alkylene, cycloalkylene, alkenylene, alkynylene, arylene, aralkylene, heterocyclylalkylene, or heterocyclylene group as defined herein. R ³³ and R ³⁴ are independently hydrogen or a substituted or unsubstituted alkyl, cycloalkyl, alkenyl, alkynyl, aryl, aralkyl, heterocyclylalkyl, or heterocyclyl group as defined herein .

As used herein, the term "amine" also refers to an independent chemical compound. When the amine is a compound, it can be represented by the formula R ^32' NR ^33' R ^34' group, where R ^32', R ^33' and R ³⁴ are independently hydrogen, or A substituted or unsubstituted alkyl, cycloalkyl, alkenyl, alkynyl, aryl, aralkyl, heterocyclylalkyl, or heterocyclyl group, as defined.

As used herein, the term "alcohol" refers to the -R ³⁵ OH group. R ³⁵ is absent, or is a substituted or unsubstituted alkylene, cycloalkylene, alkenylene, alkynylene, arylene, aralkylene, heterocyclylalkylene, or heterocyclylene group as defined herein.

As used herein, the term “carboxylic acid” refers to the —R ³⁶ COOH group. R ³⁶ is absent, substituted or unsubstituted alkylene, cycloalkylene, alkenylene, alkynylene, arylene, aralkylene, heterocyclylalkylene, or heterocyclylene group as defined herein.

As used herein, the term “ether” refers to the —R ³⁷ OR ³⁸ group. R ³⁷ is absent, substituted or unsubstituted alkylene, cycloalkylene, alkenylene, alkynylene, arylene, aralkylene, heterocyclylalkylene, or heterocyclylene group as defined herein. R ³⁸ is a substituted or unsubstituted alkyl, cycloalkyl, alkenyl, alkynyl, aryl, aralkyl, heterocyclylalkyl, or heterocyclyl group as defined herein.

The term "solvent" as used herein refers to any inorganic or organic solvent. Solvents are useful in the disclosed methods or articles, products, or compositions as reaction solvents or carrier solvents. Suitable solvents include, but are not limited to, oxygenated solvents such as lower alkanols, lower alkyl ethers, glycols, aryl glycol ethers, and lower alkyl glycol ethers. Examples of other solvents include methanol, ethanol, propanol, isopropanol and butanol, isobutanol, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, hexylene glycol, mixed ethylene-propylene glycol ethers, ethylene glycol. Examples include, but are not limited to, phenyl ether, and propylene glycol phenyl ether. Water is also a solvent. A solvent used herein can be a single solvent or a mixture of many different solvents.

Glycol ethers include diethylene glycol n-butyl ether, diethylene glycol n-propyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, diethylene glycol t-butyl ether, dipropylene glycol n-butyl ether, dipropylene glycol methyl ether, dipropylene glycol ethyl ether, and dipropylene. Glycol propyl ether, dipropylene glycol tert-butyl ether, ethylene glycol butyl ether, ethylene glycol propyl ether, ethylene glycol ethyl ether, ethylene glycol methyl ether, ethylene glycol methyl ether acetate, propylene glycol n-butyl ether, propylene glycol ethyl ether, propylene glycol methyl Ethers, propylene glycol n-propyl ether, tripropylene glycol methyl ether and tripropylene glycol n-butyl ether, ethylene glycol phenyl ether, propylene glycol phenyl ether, etc., or mixtures thereof.

式中、
Ｘは、ＮＨまたはＯであり、
Ｒ^１１は、Ｒ^１またはＲ^１－Ｚ－（ＣＨ_２）_ｍ－であり、
Ｒ^１は、非置換もしくは置換の直鎖もしくは分岐鎖Ｃ_１～Ｃ_３０アルキル、環状アルキル、アルケニル、またはアルキニル基であり、
Ｚは、ＮＨまたはＯであり、
Ｒ^２は、Ｈ、ＣＨ_３、または非置換の直鎖もしくは分岐鎖Ｃ_２～Ｃ_１０アルキル、アルケニル、もしくはアルキニル基であり、
ｍは、１～４の整数であり、
Ｒ^３は、存在しないか、または非置換の直鎖Ｃ_{１～Ｃ３０}アルキレン基であり、
Ｙは、－ＮＲ^４Ｒ^５Ｒ^６（＋）またはその塩であり、
Ｒ^４、Ｒ^５、およびＲ^６は独立して、Ｃ_１～Ｃ_１０アルキル基である。 In one aspect, disclosed herein are compounds according to Formula I,

During the ceremony,
X is NH or O;
R ¹¹ is R ¹ or R ¹ -Z-(CH ₂ ) _m -;
R ¹ is an unsubstituted or substituted straight or branched chain C ₁ -C ₃₀ alkyl, cyclic alkyl, alkenyl, or alkynyl group;
Z is NH or O;
R ² is H, CH ₃ , or an unsubstituted straight or branched chain C ₂ -C ₁₀ alkyl, alkenyl, or alkynyl group;
m is an integer from 1 to 4,
R ³ is absent or an unsubstituted linear C1 _-C30 alkylene group;
Y is -NR ⁴ R ⁵ R ^{6 (+)} or a salt thereof;
R ⁴ , R ⁵ and R ⁶ are independently C ₁ -C ₁₀ alkyl groups.

In some embodiments of the compounds disclosed herein, X is NH. In some other embodiments, X is O.

In some embodiments, R ¹¹ is R ¹ . In some other embodiments, R ¹¹ is R ¹ -Z-(CH ₂ ) _m -. In some embodiments, R ¹¹ is R ¹ -Z-(CH ₂ ) _m - and Z is NH. In some other embodiments, R ¹¹ is R ¹ -Z-(CH ₂ ) _m - and Z is O. In still some other embodiments, R ¹¹ is R ¹ -Z-(CH ₂ ) _m -, Z is NH and m is 2.

In some embodiments, ^R2 is H. In some embodiments, ^R2 is _CH3 . In still some other embodiments, R ² is CH ₃ CH ₃ , CH ₂ CH ₂ CH ₃ , or CH(CH ₃ ) ₂ .

In some embodiments, Y is -NR ⁴ R ⁵ R ⁶⁽⁺⁾ . In some other embodiments, Y is -NR ⁴ R ⁵ R ⁶⁽⁺⁾ and R ⁴ , R ⁵ and R ⁶ are independently CH ₃ . In still some other embodiments, Y is -NR ⁴ R ⁵ R ⁶⁽⁺⁾ , R ⁴ and R ⁵ are independently CH ₃ and R ⁶ is C ₆ -C ₁₂ Aromatic alkyl. In some other embodiments, Y is -NR ⁴ R ⁵ R ⁶⁽⁺⁾ , R ⁴ and R ⁵ are independently CH ₃ and R ⁶ is -CH ₂ -C _{6 H5} .

In some embodiments, Y is -NR ⁴ R ⁵ R ⁶⁽⁺⁾ and the counterion of Y is a negatively charged ion or species. In some other embodiments, the counterion for Y is chloride, bromide, fluoride, iodide, acetate, aluminate, cyanate, cyanide, dihydrogen phosphate, diphosphite hydrogen, formate, carbonate, hydrogen carbonate, hydrogen oxalate, hydrogen sulfate, hydroxide, nitrate, nitrite, thiocyanate, or combinations thereof.

^In some embodiments, R3 is _CH2 . _In some other embodiments, _R3 is ^CH2CH2 . In another embodiment, R3 is _C ( ^CH3 ) ₂ . In still some other embodiments, R ³ is an unsubstituted, straight chain, and saturated C ₂ -C ₁₀ alkylene group. In some embodiments, R ³ is an unsubstituted, straight chain, and unsaturated C ₂ -C ₁₀ alkylene group.

In some embodiments, R ¹ is a straight chain C ₁ -C ₃₀ alkyl, alkenyl, or alkynyl group. In some other embodiments, R ¹ is a branched C ₁ -C ₃₀ alkyl, alkenyl, or alkynyl group. In still some other embodiments, R ¹ is a linear and saturated C ₅ -C ₃₀ alkyl group. In some other embodiments, R ¹ is a branched and saturated C ₅ -C ₃₀ alkyl group.

In some embodiments, R ¹ is a straight chain C ₁ -C ₃₀ alkenyl group having one or more double bonds. In some other embodiments, R ¹ is a branched C ₁ -C ₃₀ alkenyl group having one or more double bonds.

In some embodiments, R ¹ is a straight chain C ₁ -C ₃₀ alkynyl group having one or more triple bonds. In some other embodiments, R ¹ is a branched C ₁ -C ₃₀ alkynyl group having one or more triple bonds.

In some embodiments, R ¹¹ is a straight chain and saturated C ₂ -C ₂₀ alkyl group. In some other embodiments, R ¹¹ is a trans C ₂ -C ₂₀ alkenyl group having at least one double bond. In some other embodiments, R ¹¹ is a C ₂ -C ₂₀ alkenyl group having at least one double bond in trans configuration. In some embodiments, R ¹¹ is a cis C ₂ -C ₂₀ alkenyl group having at least one double bond. In some other embodiments, R ¹¹ is a C ₂ -C ₂₀ alkenyl group having at least one double bond in a cis configuration.

In some embodiments, R ¹¹ is a R ¹ —NH—CH ₂ CH ₂ CH ₂ group and R ¹ is a linear and saturated C ₂ -C ₂₀ alkyl, transalkenyl, or cisalkenyl group .

In some other embodiments, R ² is H, X is NH, R ³ is CH ₂ CH ₂ and Y is -N ⁺ (CH ₃ ) ₃ Cl ^- .

式中、Ｘは、ＮＨまたはＯであり、Ｒ^１１は、Ｒ１またはＲ^１－Ｚ－（ＣＨ_２）_ｍ－であり、Ｒ^１は、非置換もしくは置換の直鎖もしくは分岐鎖Ｃ_１～Ｃ_３０アルキル、環状アルキル、アルケニル、またはアルキニル基であり、Ｚは、ＮＨまたはＯであり、Ｒ^２は、Ｈ、ＣＨ_３、または非置換の直鎖もしくは分岐鎖Ｃ_１～Ｃ_１０アルキル、アルケニル、またはアルキニル基であり、Ｒ^２’は、Ｈ、ＣＨ_３、または非置換もしくは置換の直鎖もしくは分岐鎖Ｃ_１～Ｃ_１０アルキル、アルケニル、アルキニル基、－ＣＯＯＨ、－ＣＨ_２ＣＯＯＨ、Ｙ’、または－（ＣＨ_２）_ｍ－Ｙ’であり、ｍは、１～４の整数であり、Ｒ^３は、存在しないか、または非置換の直鎖Ｃ_１～Ｃ_３０アルキレン基であり、Ｙ’は、－ＣＯＯＨ、－ＰＯ_３Ｈ、－ＯＰＯ_３Ｈ、－ＳＯ_３Ｈ、－ＯＳＯ_３Ｈ、またはそれらの塩である。 In another aspect, disclosed herein are compounds according to Formula II or Formula III,

wherein X is NH or O, R ¹¹ is R1 or R ¹ -Z-(CH ₂ ) _m -, and R ¹ is unsubstituted or substituted straight or branched chain C ₁ -C ₃₀ alkyl, cyclic alkyl, alkenyl, or alkynyl group, Z is NH or O, R ² is H, CH ₃ , or unsubstituted straight or branched chain C ₁ -C ₁₀ alkyl, alkenyl, or an alkynyl group, where R ^2′ is H, CH ₃ , or an unsubstituted or substituted straight or branched chain C ₁ -C ₁₀ alkyl, alkenyl, alkynyl group, —COOH, —CH ₂ COOH, Y′, or -(CH ₂ ) _m -Y', where m is an integer from 1 to 4, R ³ is absent or an unsubstituted linear C ₁ -C ₃₀ alkylene group, and Y' is -COOH, -PO ₃ H, -OPO ₃ H, -SO ₃ H, -OSO ₃ H, or salts thereof.

In some embodiments, Y' is -COOH or a salt thereof. In some embodiments, Y' is -PO ₃ H, -OPO ₃ H, or a salt thereof. In some other embodiments, Y' is -SO ₃ H, -OSO ₃ H, or a salt thereof.

In some embodiments of the compounds disclosed herein, X is NH. In some other embodiments, X is O.

In some embodiments, R ¹¹ is R ¹ . In some other embodiments, R ¹¹ is R ¹ -Z-(CH ₂ ) _m -. In some embodiments, R ¹¹ is R ¹ -Z-(CH ₂ ) _m - and Z is NH. In some other embodiments, R ¹¹ is R ¹ -Z-(CH ₂ ) _m - and Z is O. In still some other embodiments, R ¹¹ is R ¹ -Z-(CH ₂ ) _m -, Z is NH and m is 2.

In some embodiments, ^R2 is H. In some embodiments, ^R2 is _CH3 . In still some other embodiments, R ² is CH ₃ CH ₃ , CH ₂ CH ₂ CH ₃ , or CH(CH ₃ ) ₂ .

In some embodiments, R ^2' is H. In some embodiments, R ^2' is CH ₃ . In still some other embodiments, R ^2′ is CH ₃ CH ₃ , CH ₂ CH ₂ CH ₃ , or CH(CH ₃ ) ₂ . In some other embodiments, R ^2' is -COOH. In some other embodiments, R ^2' is -CH ₂ COOH.

^In some embodiments, R3 is _CH2 . _In some other embodiments, _R3 is ^CH2CH2 . In another embodiment, R3 is _C ( ^CH3 ) ₂ . In still some other embodiments, R ³ is an unsubstituted, straight chain, and saturated C ₂ -C ₁₀ alkylene group. In some embodiments, R ³ is an unsubstituted, straight chain, and unsaturated C ₂ -C ₁₀ alkylene group.

In some embodiments, R ¹ is a straight chain C ₁ -C ₃₀ alkyl, alkenyl, or alkynyl group. In some other embodiments, R ¹ is a branched C ₁ -C ₃₀ alkyl, alkenyl, or alkynyl group. In still some other embodiments, R ¹ is a linear and saturated C ₅ -C ₃₀ alkyl group. In some other embodiments, R ¹ is a branched and saturated C ₅ -C ₃₀ alkyl group.

In some embodiments, R ¹ is a straight chain C ₁ -C ₃₀ alkenyl group having one or more double bonds. In some other embodiments, R ¹ is a branched C ₁ -C ₃₀ alkenyl group having one or more double bonds.

In some embodiments, R ¹ is a straight chain C ₁ -C ₃₀ alkynyl group having one or more triple bonds. In some other embodiments, R ¹ is a branched C ₁ -C ₃₀ alkynyl group having one or more triple bonds.

In some embodiments, R ¹¹ is a straight chain and saturated C ₂ -C ₂₀ alkyl group. In some other embodiments, R ¹¹ is a trans C ₂ -C ₂₀ alkenyl group having at least one double bond. In some other embodiments, R ¹¹ is a C ₂ -C ₂₀ alkenyl group having at least one double bond in trans configuration. In some embodiments, R ¹¹ is a cis C ₂ -C ₂₀ alkenyl group having at least one double bond. In some other embodiments, R ¹¹ is a C ₂ -C ₂₀ alkenyl group having at least one double bond in a cis configuration.

In some embodiments, R ¹¹ is a R ¹ —NH—CH ₂ CH ₂ CH ₂ group and R ¹ is a linear and saturated C ₁ -C ₂₀ alkyl, transalkenyl, or cisalkenyl group .

In some other embodiments, R ² is H, X is NH, R ³ is CH ₂ CH ₂ and Y' is -COOH or -PO ₃ H. In some embodiments, the compound is according to Formula II. In some other embodiments, the compound is according to Formula III.

In some embodiments, the compound is of formula III, R ^2' is H, X is NH, and Y' is -COOH or -PO ₃ H. In some other embodiments, the compound is of formula III, R ^2' is -CH ₃ , X is NH, Y' is -COOH or -PO ₃ H be. In still some other embodiments, the compound has Formula III, R ^2' is Y' or -CH ₂ Y', X is NH, Y' is -COOH or _-PO3H .

In still some other embodiments, when the compound has Formula III and the Y′ group is negatively charged, the negatively charged counter cations include alkali metal ions, Li ⁺ , Na ⁺ , K ⁺ , NH ₄ ⁺ , quaternary ammonium ions, and the like.

Without being limited to a particular mechanism of action or definition of compound structure and function, the compounds disclosed herein have two hydrophilic groups associated with one hydrophobic group. Accordingly, the compounds disclosed herein have a ratio of hydrophilic to hydrophobic groups of 2:1, compared to both conventional surfactants and gemini surfactants, which exhibit a 1:1 ratio. 1A, 1B, and 1C are representations of exemplary compounds disclosed herein (FIG. 1C), along with representations of conventional surfactants (FIG. 1A) and gemini surfactants (FIG. 1B). indicates The higher ratio of hydrophilic to hydrophobic groups makes the disclosed compounds useful in antibacterial disinfectants, fabric softeners, antistatic agents, corrosion inhibitors, foaming agents, flotation collectors, dispersants, surfactants. are particularly well suited for use as enhanced oil recovery (EOR) cleaners and the like.

In this disclosure, the term "hydrophobic group" may be used interchangeably with the term "hydrophobic tail or head." Similarly, the term "hydrophilic group" can be used interchangeably with the terms "polar head or tail" or "polar group." The term "molecule" can also be used interchangeably with the term "compound."

Methods of Making In another aspect, disclosed herein are methods for synthesizing the compounds disclosed herein. The disclosed method involves combining a primary amine (Michael donor) with an activated olefin containing a hydrophilic group (Michael acceptor) at a temperature of about -20°C to about 200°C, in some embodiments about 10 minutes to about 48 hours to form a compound disclosed herein. The reaction leading to the compounds disclosed herein is an aza-Michael addition between a primary amine (Michael donor) and an activated olefin containing a hydrophilic group (Michael acceptor).

Aliphatic amine groups can undergo aza-Michael addition reactions when contacted with unsaturated hydrocarbon moieties (e.g., carbon-carbon double bonds) near electron-withdrawing groups such as carbonyl, cyano, or nitro groups. . Specifically, a Michael addition is a reaction between a nucleophile and an activated olefin and alkyne functionality, where the nucleophile is adjacent to an electron-withdrawing group such as a carbonyl group and a resonance-stabilizing activating group. It adds across a carbon-carbon multiple bond. A Michael addition nucleophile is known as a "Michael donor," an activated electrophilic olefin is known as a "Michael acceptor," and the reaction product of the two components is known as a "Michael adduct." ing. Examples of Michael donors include, but are not limited to, amines, thiols, phosphines, carbanions, and alkoxides. Examples of Michael acceptors include acrylates, alkyl methacrylates, acrylonitrile, acrylamides, maleimides, cyanoacrylates and vinyl sulfones, vinyl ketones, nitroethylenes, α,β-unsaturated aldehydes, vinyl phosphonates, acrylonitrile, vinylpyridine, Non-limiting examples include azo compounds, beta-ketoacetylenes, and acetylenic esters.

As used herein, "activated olefin" refers to a substituted alkene in which at least one of the double-bonded carbons has a conjugated electron-withdrawing group. Examples of activated olefins include α,β-unsaturated carbonyl compounds (CH ₂ ═CHCO—NH—CH ₃ , alkyl-CH═CH—CO-alkyl, CH ₂ ═CH ₂ C(O)—O—CH ₃ ), CH ₂ =CH-COOH, CH ₂ =CH(CH ₃ )-COOH, CH ₂ =CH-SO ₃ H, etc.).

As used herein, "contacting" means a primary amine (Michael donor) and at least one cationic group or Refers to any method for bringing together activated olefins (Michael acceptors) containing anionic groups. For example, in some embodiments, a primary amine or solution comprising a primary amine can be added batchwise or dropwise to a vessel or vessel containing an activated olefin or solution comprising an activated olefin. In some other embodiments, the activated olefin or solution comprising the activated olefin may be added batchwise or dropwise to a vessel or vessel containing the primary amine or solution comprising the primary amine. In yet some other embodiments, both the activated olefin or the solution comprising the activated olefin and the primary amine or solution comprising the primary amine are added to the vessel or vessel in batch or dropwise simultaneously, continuously, or alternatively. is added to

The chemical reaction used to synthesize the disclosed compounds is an aza-Michael addition reaction. It has been found that the aza-Michael addition can be used to synthesize the disclosed compounds under mild conditions and in high yields of the disclosed compounds under moderate reaction times.

Aza-Michael addition reactions can be catalyzed by strong acids or strong bases. In some cases, some ionic liquids can function as both reaction media and catalysts. Preferred catalysts for the aza-Michael addition reaction to synthesize the disclosed compounds are bases. The base catalyst can be either or a combination of alkalinity sources or primary alkalinity sources. Exemplary base catalysts can be alkali metals, hydroxides, alkali metal carbonates, alkali metal silicates, alkali metal silicates, or amines. Exemplary base catalysts can be hydroxides and amines. Because the reactions for synthesizing the disclosed compounds use primary amines, the primary amines themselves can serve as catalysts for the reaction. In such embodiments, no additional catalyst is required or optional. Other preferred catalysts include amidine and guanidine bases.

The use of solvents and/or diluents for the reaction is optional. When used, for example water, ethers (eg tetrahydrofuran (THF)), aromatic hydrocarbons (eg toluene and xylene), alcohols (eg n-butanol), esters (eg ethyl 3-ethoxypropionate) A variety of non-acidic solvents such as are suitable. A variety of solvents can be used for the reaction, as the synthetic process is relatively solvent insensitive. If a solvent (or diluent) is used, loading levels can range from about 0 weight percent up to about 80 weight percent or more. Solvent loading levels range from about 0%, from about 1% to about 10%, from about 10% to about 20%, from about 20% to about 30%, from about 30% to about 10%, by weight of the final reaction mixture. 40 wt%, about 40 wt% to about 50 wt%, about 50 wt% to about 60 wt%, about 60 wt% to about 70 wt%, about 70 wt% to about 80 wt%, about 1 wt% to about 20 wt%, about 20 wt% to about 40 wt%, about 40 wt% to about 60 wt%, about 60 wt% to about 80 wt%, about 40 wt% to about 70 wt%, about 5 wt%, about It can be 15 wt%, about 25 wt%, 35 wt%, about 45 wt%, about 55 wt%, about 65 wt%, about 75 wt%, or any value therebetween.

Generally, the contacting step of the method can be performed at temperatures over a wide range of temperatures. The contact or reaction temperature can range from about -20°C to about 200°C, from about 0 ^° C to about 150 ^° C, more preferably from about 50 ^° C to about 80 ^° C. Contact temperatures range from about 10 ^° C. to about 140 ^° C., from about 20 ^° C. to about 130 ^° C., from about 30 ^° C. to about 120 ^° C., from about 40 ^° C. to about 110 ^° C., from about 50 ^° C. to about 100 ^° C., about 60 ^° C. to about 90 ^° C., about 70 ^° C. to about 80 ^° C., about 0 ^° C. to about 20 ^° C., about 20 ^° C. to about 40 ^° C., about 40 ^° C. to about 60 ^° C., about 60 ^° C. to about 80 ^° C., about 80 ^° C. to about 100 ^° C., about 100 ^° C. to about 120 ^° C., about 120 ^° C. to about 150 ^° C., about 5 ^° C., about It can be 25 ^° C., about 45 ^° C., about 65 ^° C., about 85 ^° C., about 105 ^° C., about 125 ^° C., about 145 ^° C., or any value therebetween. The reaction temperature can be about the same from the beginning of the reaction to the end of the reaction, and can be changed from one temperature to another during the course of the reaction.

Contact or reaction times for the synthesis of the compounds disclosed herein can vary widely depending on factors such as reaction temperature, catalyst effectiveness and amount, and the presence or absence of diluent (solvent). Preferred reaction times are from about 10 minutes to about 48 hours, from about 0.5 hours to about 48 hours, from about 1 hour to 40 hours, from about 2 hours to 38 hours, from about 4 hours to about 36 hours, from 6 hours to about 34 hours. time, about 8 hours to about 32 hours, about 10 hours to about 30 hours, about 12 hours to about 28 hours, about 14 hours to 26 hours, about 16 hours to 24 hours, about 18 hours to 20 hours, about 1 hour ~8 hours, 8 hours to 16 hours, 8 hours to about 24 hours, about 2 hours, about 4 hours, about 6 hours, about 8 hours, about 10 hours, about 14 hours, about 16 hours, about 18 hours, about It can be 24 hours, about 30 hours, about 36 hours, or any value therebetween.

The reaction for the synthesis of the compounds disclosed herein can be completed when 1 mole of primary amine and at least 2 moles of activated olefin are mixed together at the above temperature for a sufficient time. Typically, the reaction can have a product yield of greater than 98% when the reaction is carried out at room temperature.

であり、Ｘは、ＮＨまたはＯであり、
Ｒ^１１は、Ｒ^１またはＲ^１－Ｚ－（ＣＨ_２）_ｍ－であり、
Ｒ^１は、非置換もしくは置換の直鎖もしくは分岐鎖Ｃ_１～Ｃ_３０アルキル、環状アルキル、アルケニル、またはアルキニル基であり、
Ｚは、ＮＨまたはＯであり、
Ｒ^２は、Ｈ、ＣＨ_３、または非置換の直鎖もしくは分岐鎖Ｃ_１～Ｃ_１０アルキル、アルケニル、もしくはアルキニル基であり、
ｍは、１～４の整数であり、
Ｒ^３は、存在しないか、または非置換の直鎖Ｃ_{１～Ｃ３０}アルキレン基であり、
Ｙは、－ＮＲ^４Ｒ^５Ｒ^６（＋）またはその塩であり、
Ｒ^４、Ｒ^５、およびＲ^６は独立して、Ｃ_１～Ｃ_１０アルキル基である。 In some embodiments of the disclosed method, the primary amine is R ¹¹ —NH ₂ , R ¹¹ is R ¹ or R ¹ —Z—(CH ₂ ) _m —, and the activated olefin is

and X is NH or O;
R ¹¹ is R ¹ or R ¹ -Z-(CH ₂ ) _m -;
R ¹ is an unsubstituted or substituted straight or branched chain C ₁ -C ₃₀ alkyl, cyclic alkyl, alkenyl, or alkynyl group;
Z is NH or O;
R ² is H, CH ₃ , or an unsubstituted straight or branched chain C ₁ -C ₁₀ alkyl, alkenyl, or alkynyl group;
m is an integer from 1 to 4,
R ³ is absent or an unsubstituted linear C1 _-C30 alkylene group;
Y is -NR ⁴ R ⁵ R ^{6 (+)} or a salt thereof;
R ⁴ , R ⁵ and R ⁶ are independently C ₁ -C ₁₀ alkyl groups.

In some embodiments, the activated olefin is (3-acrylamidopropyl)trimethylammonium chloride (APTAC), [3-(methacryloylamino)propyl]trimethylammonium chloride (MAPTAC), 2-(acryloyloxy)-N, N,N-trimethylethaneminium chloride (DMAEA-MCQ), N,N-dimethylaminoethyl acrylate benzyl chloride quaternary salt (DMAEA-BCQ), 2-(methacryloyloxy)-N,N,N-trimethylethane- 1-aminium methyl sulfate (DMAEA-MSQ), 2-(acryloyloxy)-N,N,N-trimethylethanaminium chloride (DMAEA-MCQ), or mixtures thereof.

であり、Ｘは、ＮＨまたはＯであり、
Ｒ^１１は、Ｒ^１またはＲ^１－Ｚ－（ＣＨ_２）_ｍ－であり、
Ｒ^１は、非置換もしくは置換の直鎖もしくは分岐鎖Ｃ_１～Ｃ_３０アルキル、環状アルキル、アルケニル、またはアルキニル基であり、
Ｚは、ＮＨまたはＯであり、
Ｒ^２は、Ｈ、ＣＨ_３、または非置換の直鎖もしくは分岐鎖Ｃ_１～Ｃ_１０アルキル、アルケニル、もしくはアルキニル基であり、
Ｒ^２’は、Ｈ、ＣＨ_３、または非置換もしくは置換の直鎖もしくは分岐鎖Ｃ_１～Ｃ_１０アルキル、アルケニル、アルキニル基、－ＣＯＯＨ、－ＣＨ_２ＣＯＯＨ、Ｙ’、または－（ＣＨ_２）_ｍ－Ｙ’であり、
ｍは、１～４の整数であり、
Ｒ^３は、存在しないか、または非置換の直鎖Ｃ_{１～Ｃ３０}アルキレン基であり、
Ｙ’は、－ＣＯＯＨ、－ＰＯ_３Ｈ、－ＳＯ_３Ｈ、またはそれらの塩である。 In some embodiments of the disclosed method, the primary amine is R ¹¹ —NH ₂ , R ¹¹ is R ¹ or R ¹ —Z—(CH ₂ ) _m —, and the activated olefin is

and X is NH or O;
R ¹¹ is R ¹ or R ¹ -Z-(CH ₂ ) _m -;
R ¹ is an unsubstituted or substituted straight or branched chain C ₁ -C ₃₀ alkyl, cyclic alkyl, alkenyl, or alkynyl group;
Z is NH or O;
R ² is H, CH ₃ , or an unsubstituted straight or branched chain C ₁ -C ₁₀ alkyl, alkenyl, or alkynyl group;
R ^2′ is H, CH ₃ , or an unsubstituted or substituted straight or branched chain C ₁ -C ₁₀ alkyl, alkenyl, alkynyl group, —COOH, —CH ₂ COOH, Y′, or —(CH ₂ ) _m -Y',
m is an integer from 1 to 4,
R ³ is absent or an unsubstituted linear C1 _-C30 alkylene group;
Y' is -COOH, -PO ₃ H, -SO ₃ H, or a salt thereof.

In some embodiments, the activated olefin is acrylic acid, methacrylic acid, itaconic acid, maleic acid, vinylsulfonic acid, vinylphosphonic acid, or mixtures thereof.

In some other embodiments, the activated olefin is 2-acrylamido-2-methylpropanesulfonic acid (AMPS), 3-(allyloxy)-2-hydroxypropane-1-sulfonate, or mixtures thereof.

In yet some other embodiments, when the activated olefin contains an anionic group that can be negatively charged at alkaline pH, the negatively charged counter cations include alkali metal ions, Li ⁺ , Na ⁺ , Examples include, but are not limited to, K ⁺ , NH ₄ ⁺ , quaternary ammonium ions, and the like.

In some embodiments of the disclosed method, the contacting step is performed in the presence of a reaction solvent. The reaction solvent can be any inorganic or organic solvent commonly used in chemical synthesis. The reaction solvent used in the disclosed method can be introduced into the reaction between the primary amine and the activated olefin containing cationic or anionic groups by any method known to those skilled in the art. For example, a solvent can be added to the reaction vessel or vessel before the primary amine, activated olefin, or both are added, simultaneously with one or both reactants, or after.

In some embodiments, the reaction solvent is water, methanol, ethanol, propanol, glycol, PEG, or mixtures thereof. In some other embodiments, the reaction solvent is water.

In some other embodiments of the disclosed method, the contacting step is performed in the presence of a catalyst, base, or acid. A catalyst, base, or acid may be introduced into the reaction between the primary amine and the activated olefin by any method known to those skilled in the art.

In some embodiments, the contacting step is performed without the presence of any additional base. In some other embodiments, the contacting step is performed in the presence of an alkalinity source. In some other embodiments, the contacting step is performed in the presence of an organic base such as an alkanolamine. In yet some other embodiments, the contacting step comprises alkali metal hydroxides, carbonates, imidazole/pyridine bases, or combinations thereof, such as NaOH, _{Na2CO3 ,} aminoethylpyridine, aminopropylimidazole. , or combinations thereof. In some other embodiments, the contacting step is performed in the presence of benzyltrimethylammonium hydroxide. In some embodiments, the catalytic base is an amidine or guanidine base, or mixtures thereof. In some other embodiments, the catalyst is a catalyst such as 1,8-diazabicyclo[5.4.0]-undec-7-en-8-ium acetate for reaction under solvent-free conditions at room temperature. It is an ionic liquid.

In still some other embodiments of the disclosed method, the contacting step is performed in the presence of an acid. In some other embodiments, the contacting step is performed in the presence of a catalyst. The catalyst can be any one or more of the catalysts known to those skilled in the art for Michael addition reactions.

In still some other embodiments of the disclosed method, the contacting step is performed without a catalyst, base, or acid. In some other embodiments, the contacting step is performed without alkali metal hydroxides, carbonates, silicates, metasilicates, imidazole/pyridine bases, or all of them. In some embodiments, the contacting step is performed without a base.

In yet another aspect, disclosed herein are articles, products, or compositions comprising one or more compounds disclosed herein or produced by the methods disclosed herein. be.

In some embodiments, the article, product, or composition further comprises a carrier solvent or carrier. As used herein, a "carrier solvent" or carrier is a solvent or solvent system in which the disclosed compounds can be uniformly distributed and stabilized.

As used herein, "stable" means that the compounds disclosed herein are stable after the compounds disclosed herein and carrier solvent or any other ingredients are homogeneously mixed. about 1 hour, about 1 hour to about 12 hours, about 12 hours, about 1 day, about 5 days, about 10 days, about 20 days, about 1 month, about 1 month to about 1 year, or about 1 year to about Two years means no precipitation or separation from the carrier solvent or other ingredients in the composition.

In some embodiments, the carrier solvent can be any inorganic or organic solvent commonly used in industry or in the laboratory. In some other embodiments of the article, manufacture, or composition, the carrier solvent is water, alcohol, alkylene glycol, alkylene glycol alkyl ether, or combinations thereof. In some other embodiments, the carrier solvent is methanol, ethanol, propanol, isopropanol, butanol, isobutanol, monoethylene glycol, ethylene glycol monobutyl ether, or combinations thereof.

In some embodiments, the article, product, or composition is solid. In some other embodiments, the article, product, or composition is liquid.

In some embodiments, the article, product, or composition can further comprise an additional surfactant. Additional surfactants are nonionic, semi-nonionic, anionic, cationic, amphoteric, zwitterionic, gemini surfactants, or combinations thereof.

In some embodiments, the additional surfactants are nonionic, semi-nonionic, anionic, cationic, amphoteric, zwitterionic, gemini surfactants, or combinations thereof. In some embodiments, the compositions disclosed herein contain conventional surfactants but no gemini surfactants. In some other embodiments, the composition contains a gemini surfactant but no regular surfactant. In yet some other embodiments, the surfactant composition comprises one of nonionic, semi-nonionic, anionic, cationic, amphoteric, and zwitterionic surfactants. , excluding residual surfactants. For example, the disclosed compositions can include one or more compounds disclosed herein and one or more nonionic surfactants, including semi-nonionic, anionic, cationic Contains no , amphoteric, zwitterionic, or gemini surfactants.

In some embodiments, an article, manufacture, or composition disclosed herein comprises one or more compounds disclosed herein, an acid, and a carrier solvent. In some embodiments, the article, manufacture, or composition disclosed herein comprises one or more compounds disclosed herein, an acid, a carrier solvent, and a peroxycarboxylic acid or peroxycarboxylic acid composition Including things.

In some embodiments, the article, product, or composition can further comprise a primary source of alkalinity. In some embodiments, the articles, products, or compositions disclosed herein are detergent compositions comprising one or more compounds disclosed herein and a primary alkalinity source. Detergent compositions, as used herein, contain more primary alkalinity source in weight percent than the compounds disclosed herein and have a use solution pH of about 8 to about 13. It refers to a composition that can form a solution.

In some embodiments, the article, product, or composition disclosed herein is a detergent composition comprising one or more compounds disclosed herein, a primary alkalinity source, and a chelating agent. . In some embodiments, the article, product, or composition disclosed herein is a detergent comprising one or more compounds disclosed herein, a primary alkalinity source, a chelating agent, and a surfactant. composition. In some embodiments, an article, product, or composition disclosed herein comprises one or more compounds disclosed herein, a primary alkalinity source, and a chelating agent, but without a surfactant is a detergent composition that does not contain

In some embodiments, the composition is a solid composition. In some other embodiments, the composition is liquid.

In some embodiments, an article, product, or composition disclosed herein is a detergent composition comprising one or more compounds disclosed herein, a primary alkalinity source, and an enzyme. In some embodiments, the articles, products, or compositions disclosed herein contain one or more compounds disclosed herein, primary alkalinity sources, chelating agents, enzymes, and surfactants. A detergent composition comprising: In some embodiments, an article, product, or composition disclosed herein comprises one or more of the compounds disclosed herein, a primary alkalinity source, and an enzyme, but a surfactant, A detergent composition that does not contain a chelating agent, or both.

In some embodiments, the primary alkalinity source is an alkali metal hydroxide, alkali metal carbonate, alkali metal silicate, alkali metal silicate, amine, or Contains mixtures. In some other embodiments, the primary alkalinity source comprises alkali metal hydroxides, alkali metal carbonates, or mixtures thereof.

In some embodiments, the detergent compositions disclosed herein comprise builders. In some embodiments, the detergent compositions disclosed herein are builder-free, but contain a portion of the primary alkalinity source as a builder.

In some embodiments, the detergent compositions disclosed herein comprise an enzyme, wherein the enzyme is amylase, protease, lipase, cellulase, cutinase, gluconase, peroxidase, and/or mixtures thereof. In some embodiments the enzyme is a protease enzyme. In some embodiments, enzymes are proteases and amylases. In some other embodiments, the enzymes are proteases, amylases, and lipases. In yet some other embodiments, the detergent compositions or compositions disclosed herein do not contain enzymes.

In some embodiments, the detergent composition or composition disclosed herein comprises a chelating agent, wherein the chelating agent is methylglycine diacetic acid (MGDA), glutamic acid-N,N-diacetic acid (GLDA) , N-hydroxyethylaminodiacetic acid, ethylenediaminetetraacetic acid (EDTA) (including tetrasodium EDTA), hydroxyethylenediaminetetraacetic acid, diethylenetriaminepentaacetic acid, N-hydroxyethyl-ethylenediaminetriacetic acid (HEDTA), diethylenetriaminepentaacetic acid (DTPA) , ethylenediaminesuccinic acid (EDDS), 2-hydroxyethyliminodiacetic acid (HEIDA), iminodisuccinic acid (IDS), 3-hydroxy-2-2'-iminodisuccinic acid (HIDS), or mixtures thereof.

In other embodiments, the detergent compositions disclosed herein further comprise one or more additional detergent composition agents.

In some embodiments, the detergent compositions disclosed herein are solid compositions. In some other embodiments, the detergent composition is liquid. In some embodiments, the solid detergent composition disclosed herein is any pressed, extruded, or cast solid composition, or loose powder form. In some other embodiments, the solid detergent composition is a pressed and/or extruded block. In some other embodiments, the detergent composition is a multi-use pressed solid block composition.

Multipurpose solid block detergent compositions are preferred because they provide solid state stability and can be used in dispensers. Solidification technology and the use of solid block detergents for institutional and industrial operations, such as SOLID POWER®, as disclosed in US Reissue Patent Nos. 32,762 and 32,818. Described in terms of brand technology. In some embodiments, the detergent compositions disclosed herein are those of Heile et al. including sodium carbonate hydrate cast solid products disclosed by U.S. Pat. Each of these references is incorporated herein by reference in its entirety. Without being limited by the mechanism of action, the setting mechanism is ash hydration or the interaction of sodium carbonate with water.

Provided herein are methods of using a new class of dicationic or dianionic compounds for controlling corrosion on surfaces in aqueous systems, and corresponding corrosion control compositions containing this new class of dicationic or dianionic compounds. Articles are also disclosed herein. Specifically, it contains two identical hydrophilic groups and one hydrophobic group and is derived from an aza-Michael addition reaction between a primary amine (Michael donor) and an activated olefin (Michael acceptor). The use of one or more dicationic or dianionic compounds as corrosion control agents is disclosed.

式中、Ｘは、ＮＨまたはＯであり、Ｒ^１１は、Ｒ１またはＲ^１－Ｚ－（ＣＨ_２）_ｍ－であり、Ｒ^１は、非置換もしくは置換の直鎖もしくは分岐鎖Ｃ_１～Ｃ_３０アルキル、環状アルキル、アルケニル、またはアルキニル基であり、Ｚは、ＮＨまたはＯであり、Ｒ^２は、Ｈ、ＣＨ_３、または非置換の直鎖または分岐鎖Ｃ_２～Ｃ_１０アルキル、アルケニル、またはアルキニル基であり、ｍは、１～４の整数であり、Ｒ^３は、存在しないか、または非置換の直鎖Ｃ_１～Ｃ_３０アルキレン基であり、Ｙは、－ＮＲ^４Ｒ^５Ｒ^６（＋）であり、Ｙ’は、－ＣＯＯＨ、－ＳＯ_３Ｈ、－ＰＯ_３Ｈ、－ＯＳＯ_３Ｈ、－ＯＰＯ_３Ｈ、またはそれらの塩であり、Ｒ^２’は、Ｈ、ＣＨ^３、または非置換もしくは置換の直鎖もしくは分岐鎖Ｃ_１～Ｃ_１０アルキル、アルケニル、アルキニル基、－ＣＯＯＨ、－ＣＨ^２ＣＯＯＨ、Ｙ’、または－（ＣＨ_２）_ｍ－Ｙ’であり、Ｒ^４、Ｒ^５、およびＲ^６は独立して、Ｃ_１～Ｃ_１０アルキル基であり、腐食制御組成物は、水系中の表面上の腐食を緩和する。 In one aspect, corrosion control compositions are disclosed herein comprising one or more compounds according to one of Formula I, Formula II, Formula III and one or more additional corrosion control compounds. and a composition agent;

wherein X is NH or O, R ¹¹ is R1 or R ¹ -Z-(CH ₂ ) _m -, and R ¹ is unsubstituted or substituted straight or branched chain C ₁ -C ₃₀ alkyl, cyclic alkyl, alkenyl, or alkynyl group, Z is NH or O, R ² is H, CH ₃ , or unsubstituted straight or branched chain C ₂ -C ₁₀ alkyl, alkenyl, or an alkynyl group, m is an integer from 1 to 4, R ³ is absent or an unsubstituted linear C ₁ -C ₃₀ alkylene group, and Y is —NR ⁴ R ⁵ R ⁶⁽⁺⁾ , Y′ is —COOH, —SO ₃ H, —PO ₃ H, —OSO ₃ H, —OPO ₃ H, or salts thereof, R ^2′ is H, CH ³ , or an unsubstituted or substituted straight or branched chain C ₁ -C ₁₀ alkyl, alkenyl, alkynyl group, —COOH, —CH ² COOH, Y′, or —(CH ₂ ) _m —Y′, and R ⁴ , R ⁵ , and R ⁶ are independently C ₁ -C ₁₀ alkyl groups, and the corrosion control composition moderates corrosion on surfaces in aqueous systems.

式中、Ｘは、ＮＨまたはＯであり、Ｒ^１１は、Ｒ１またはＲ^１－Ｚ－（ＣＨ_２）_ｍ－であり、Ｒ^１は、非置換もしくは置換の直鎖もしくは分岐鎖Ｃ_５～Ｃ_３０アルキル、環状アルキル、アルケニル、またはアルキニル基であり、Ｚは、ＮＨまたはＯであり、Ｒ^２は、Ｈ、ＣＨ_３、または非置換の直鎖または分岐鎖Ｃ_２～Ｃ_１０アルキル、アルケニル、またはアルキニル基であり、ｍは、１～４の整数であり、Ｒ^３は、存在しないか、または非置換の直鎖Ｃ_１～Ｃ_３０アルキレン基であり、Ｙは、－ＮＲ^４Ｒ^５Ｒ^６（＋）であり、Ｙ’は、－ＣＯＯＨ、－ＳＯ_３Ｈ、－ＰＯ_３Ｈ、－ＯＳＯ_３Ｈ、－ＯＰＯ_３Ｈ、またはそれらの塩であり、Ｒ^２’は、Ｈ、ＣＨ^３、または非置換もしくは置換の直鎖もしくは分岐鎖Ｃ_１～Ｃ_１０アルキル、アルケニル、アルキニル基、－ＣＯＯＨ、－ＣＨ^２ＣＯＯＨ、Ｙ’、または－（ＣＨ_２）_ｍ－Ｙ’であり、Ｒ^４、Ｒ_５、およびＲ_６は独立して、Ｃ_１～Ｃ_１０アルキル基であり、腐食制御組成物は、水系中の表面上の腐食を緩和する。 In another aspect, disclosed herein is a method for inhibiting corrosion on a surface in an aqueous system, the method comprising providing a corrosion control composition or a use solution of the corrosion control composition into the aqueous system to treat the forming a water-based system or providing on a surface of the water-based system, the corrosion control composition comprising one or more compounds according to one of Formula I, Formula II, Formula III; an additional corrosion control composition corrosion control composition agent of

wherein X is NH or O, R ¹¹ is R1 or R ¹ -Z-(CH ₂ ) _m -, and R ¹ is unsubstituted or substituted straight or branched chain C ₅ -C ₃₀ alkyl, cyclic alkyl, alkenyl, or alkynyl group, Z is NH or O, R ² is H, CH ₃ , or unsubstituted straight or branched chain C ₂ -C ₁₀ alkyl, alkenyl, or an alkynyl group, m is an integer from 1 to 4, R ³ is absent or an unsubstituted linear C ₁ -C ₃₀ alkylene group, and Y is —NR ⁴ R ⁵ R ⁶⁽⁺⁾ , Y′ is —COOH, —SO ₃ H, —PO ₃ H, —OSO ₃ H, —OPO ₃ H, or salts thereof, R ^2′ is H, CH ³ , or an unsubstituted or substituted straight or branched chain C ₁ -C ₁₀ alkyl, alkenyl, alkynyl group, —COOH, —CH ² COOH, Y′, or —(CH ₂ ) _m —Y′, and R ⁴ , R ₅ , and R ₆ are independently C ₁ -C ₁₀ alkyl groups, and the corrosion control composition moderates corrosion on surfaces in aqueous systems.

In some embodiments, the corrosion control composition has about 2 ppm of the dicationic or dianionic compound and exhibits corrosion on metal surfaces of about 280 mpy, about 265 mpy, about It can be relaxed to 250 mpy, about 225 mpy, about 200 mpy, about 175 mpy, about 150 mpy, about 175 mpy, about 100 mpy, or any value therebetween.

In some embodiments, the one or more compounds are one or more of Formula I. In some other embodiments, one or more compounds are one or more of Formula II. In yet some other embodiments, one or more compounds are one or more of Formula III. In some other embodiments, the one or more compounds are one or more of Formula II and Formula III.

In some embodiments of the compounds disclosed herein, X is NH. In some other embodiments, X is O.

In some embodiments, R ¹¹ is R ¹ . In some other embodiments, R ¹¹ is R ¹ -Z-(CH ₂ ) _m -. In some embodiments, R ¹¹ is R ¹ -Z-(CH ₂ ) _m - and Z is NH. In some other embodiments, R ¹¹ is R ¹ -Z-(CH ₂ ) _m - and Z is O. In still some other embodiments, R ¹¹ is R ¹ -Z-(CH ₂ ) _m -, Z is NH and m is 2.

In some embodiments, ^R2 is H. In some embodiments, ^R2 is _CH3 . In still some other embodiments, R ² is CH ₃ CH ₃ , CH ₂ CH ₂ CH ₃ , or CH(CH ₃ ) ₂ .

In some embodiments, Y is -NR ⁴ R ⁵ R ⁶⁽⁺⁾ . In some other embodiments, Y is -NR ⁴ R ⁵ R ⁶⁽⁺⁾ and R ⁴ , R ⁵ and R ⁶ are independently CH ₃ . In still some other embodiments, Y is -NR ⁴ R ⁵ R ⁶⁽⁺⁾ , R ⁴ and R ⁵ are independently CH ₃ and R ⁶ is C ₂ -C ₁₂ Aromatic alkyl. In some other embodiments, Y is -NR ⁴ R ⁵ R ⁶⁽⁺⁾ , R ⁴ and R ⁵ are independently CH ₃ and R ⁶ is -CH ₂ -C _{6 H5} .

In some embodiments, Y is -NR ⁴ R ⁵ R ⁶⁽⁺⁾ and the counterion of Y is a negatively charged ion or species. In some other embodiments, the counterion for Y is chloride, bromide, fluoride, iodide, acetate, aluminate, cyanate, cyanide, dihydrogen phosphate, diphosphite hydrogen, formate, carbonate, hydrogen carbonate, hydrogen oxalate, hydrogen sulfate, hydroxide, nitrate, nitrite, thiocyanate, or combinations thereof.

In some embodiments, Y is -COOH or a salt thereof. In some other embodiments, Y is —SO ₃ H or a salt thereof. In still some other embodiments, Y is —PO ₃ H or a salt thereof. In some other embodiments, Y is an acidic species or salt thereof.

^In some embodiments, R3 is _CH2 . _In some other embodiments, _R3 is ^CH2CH2 . In another embodiment, R3 is _C ( ^CH3 ) ₂ . In still some other embodiments, R ³ is an unsubstituted, straight chain, and saturated C ₂ -C ₁₀ alkylene group. In some embodiments, R ³ is an unsubstituted, straight chain, and unsaturated C ₂ -C ₁₀ alkylene group.

In some embodiments, R ¹ is a straight chain C ₅ -C ₃₀ alkyl, alkenyl, or alkynyl group. In some other embodiments, R ¹ is a branched C ₅ -C ₃₀ alkyl, alkenyl, or alkynyl group. In still some other embodiments, R ¹ is a linear and saturated C ₅ -C ₃₀ alkyl group. In some other embodiments, R ¹ is a branched and saturated C ₅ -C ₃₀ alkyl group.

In some embodiments, R ¹ is a straight chain C ₁ -C ₃₀ alkenyl group having one or more double bonds. In some other embodiments, R ¹ is a branched C ₃ -C ₃₀ alkenyl group having one or more double bonds.

In some embodiments, R ¹ is a straight chain C ₃ -C ₃₀ alkynyl group having one or more triple bonds. In some other embodiments, R ¹ is a branched C ₃ -C ₃₀ alkynyl group having one or more triple bonds.

In some embodiments, R ¹¹ is a straight chain and saturated C ₁ -C ₂₀ alkyl group. In some other embodiments, R ¹¹ is a trans C ₃ -C ₂₀ alkenyl group having at least one double bond. In some other embodiments, R ¹¹ is a C ₃ -C ₂₀ alkenyl group having at least one double bond in trans configuration. In some embodiments, R ¹¹ is a cis C ₃ -C ₂₀ alkenyl group having at least one double bond. In some other embodiments, R ¹¹ is a C ₃ -C ₂₀ alkenyl group having at least one double bond in a cis configuration.

In some embodiments, R ¹¹ is a R ¹ —NH—CH ₂ CH ₂ CH ₂ group and R ¹ is a linear and saturated C ₆ -C ₂₀ alkyl, trans alkenyl, or cis alkenyl group .

In some other embodiments, R ² is H, X is NH, R ³ is CH ₂ CH ₂ and Y is -N ⁺ (CH ₃ ) ₃ Cl ^- .

In some embodiments, the compound is a mixture of two or more dicationic or anionic compounds. In some other embodiments, the compound is a single dicationic compound or a mixture thereof. In some other embodiments, the compound is a single dianionic compound or a mixture thereof. Two or more dicationic or anionic compounds differ from each other by molecule or average molecular weight, structure, or a combination thereof.

In some embodiments, the compound is a mixture of at least two different dicationic compounds derived from the same primary amine and activated olefin or from different primary amines and activated olefins.

In some embodiments, the compound is derived from a primary amine and (3-acrylamidopropyl)trimethylammonium chloride (APTAC). In some other embodiments, the compound is derived from a primary amine and [3-(methacryloylamino)propyl]trimethylammonium chloride (MAPTAC).

In some embodiments, compounds are derived from primary amines and activated olefins. In some embodiments, the activated olefin is (3-acrylamidopropyl)trimethylammonium chloride (APTAC), [3-(methacryloylamino)propyl]trimethylammonium chloride (MAPTAC), 2-(acryloyloxy)-N, N,N-trimethylethaneminium chloride (DMAEA-MCQ), N,N-dimethylaminoethyl acrylate benzyl chloride quaternary salt (DMAEA-BCQ), 2-(methacryloyloxy)-N,N,N-trimethylethane- 1-aminium methyl sulfate (DMAEA-MSQ), or 2-(acryloyloxy)-N,N,N-trimethylethanaminium chloride (DMAEA-MCQ).

In some other embodiments, the activated olefin is (3-acrylamidopropyl)trimethylammonium chloride (APTAC), [3-(methacryloylamino)propyl]trimethylammonium chloride (MAPTAC), or mixtures thereof.

In some other embodiments, the activated olefin is 2-(acryloyloxy)-N,N,N-trimethylethanaminium chloride (DMAEA-MCQ), N,N-dimethylaminoethyl acrylate benzyl chloride quaternary salt (DMAEA-BCQ), 2-(methacryloyloxy)-N,N,N-trimethylethane-1-aminium methylsulfate (DMAEA-MSQ), 2-(acryloyloxy)-N,N,N-trimethylethane aminium chloride (DMAEA-MCQ), or mixtures thereof.

In some embodiments, compounds are derived from primary amines and activated olefins. In some embodiments, the activated olefin is acrylic acid, methacrylic acid, itaconic acid, maleic acid, vinylsulfonic acid, vinylphosphonic acid, or mixtures thereof.

In some other embodiments, the activated olefin is 2-acrylamido-2-methylpropanesulfonic acid (AMPS), 3-(allyloxy)-2-hydroxypropane-1-sulfonate, or mixtures thereof.

In yet some other embodiments, when the activated olefin contains an anionic group that can be negatively charged at alkaline pH, the negatively charged counter cations include alkali metal ions, Li ⁺ , Na ⁺ , Examples include, but are not limited to, K ⁺ , NH ₄ ⁺ , quaternary ammonium ions, and the like.

In some embodiments, the compounds are soluble or dispersible in water or corrosion control compositions.

In some embodiments, the corrosion control composition comprises a carrier, and the carrier is water, an organic solvent, or mixtures thereof.

In some embodiments, the corrosion control composition further comprises an organic solvent. In some other embodiments, the corrosion control composition further comprises an organic solvent and water.

In some embodiments, the organic solvent is an alcohol, hydrocarbon, ketone, ether, alkylene glycol, glycol ether, amide, nitrile, sulfoxide, ester, or any combination thereof. In some other embodiments, the organic solvent is alcohol, alkylene glycol, alkylene glycol alkyl ether, or combinations thereof. Further, in some embodiments, the organic solvent is methanol, ethanol, propanol, isopropanol, butanol, isobutanol, monoethylene glycol, ethylene glycol monobutyl ether, or combinations thereof.

In some embodiments, the organic solvent is methanol, ethanol, propanol, isopropanol, butanol, 2-ethylhexanol, hexanol, octanol, decanol, 2-butoxyethanol, methylene glycol, ethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, ethylene glycol monobutyl ether, ethylene glycol dibutyl ether, pentane, hexane, cyclohexane, methylcyclohexane, heptane, decane, dodecane, diesel, toluene, xylene, heavy aromatics Naphtha, cyclohexanone, diisobutyl ketone, diethyl ether, propylene carbonate, N-methylpyrrolidinone, N,N-dimethylformamide, mixtures thereof with water, or any combination thereof.

In some embodiments, the corrosion control composition further comprises one or more additional corrosion inhibitors. In some embodiments, the corrosion control composition further comprises one or more additional corrosion inhibitors and a carrier. In some embodiments, the corrosion inhibitor is an imidazoline compound, a pyridinium compound, or a combination thereof.

In some embodiments, the corrosion control composition further comprises a fouling control agent. In some embodiments, the fouling control agent is a single quaternary compound.

In some embodiments, the corrosion control composition further comprises a biocide. In some embodiments, the corrosion control composition further comprises a biocide and a carrier. In some other embodiments, the corrosion control composition further comprises a biocide, a corrosion inhibitor, and a carrier.

In some embodiments, the biocide is an oxidizing biocide. In some other embodiments, the biocide is a non-oxidizing biocide. In some other embodiments, the biocide is chlorine, hypochlorite, _ClO2 , bromine, ozone, hydrogen peroxide, peracetic acid, peroxysulfuric acid, peroxycarboxylic acid, peroxycarboxylic acid composition, or A mixture of them. In some other embodiments, the biocide is glutaraldehyde, dibromonitrilopropionamide, isothiazolone, terbuthylazine, polymeric biguanides, methylenebisthiocyanate, tetrakishydroxymethylphosphonium sulfate, and combinations thereof.

In some embodiments, the corrosion control composition further comprises an organic sulfur compound. In some other embodiments, the organosulfur compound is mercaptoalkyl alcohol, mercaptoacetic acid, thioglycolic acid, 3,3′-dithiodipropionic acid, sodium thiosulfate, thiourea, L-cysteine, tert-butyl mercaptan , sodium thiosulfate, ammonium thiosulfate, sodium thiocyanate, ammonium thiocyanate, sodium metabisulfite, or combinations thereof.

In some embodiments, the corrosion control composition further comprises an acid. In some embodiments, the corrosion control composition further comprises inorganic acids, mineral acids, organic acids, or mixtures thereof. In some embodiments, the corrosion control composition comprises about 1% to about 20% by weight acid.

In some embodiments, the acid is hydrochloric acid, hydrofluoric acid, citric acid, formic acid, acetic acid, or mixtures thereof.

In some embodiments, the corrosion control composition further comprises a hydrogen sulfide scavenger. In some other embodiments, the hydrogen sulfide scavenger is an oxidizing agent, inorganic peroxide, sodium peroxide, chlorine dioxide _; C1 _- C10 aldehyde, formaldehyde, glyoxal, glutaraldehyde, acrolein or methacrolein, triazine , monoethanolamine triazine, monomethylamine triazine, or mixtures thereof.

In some embodiments, the corrosion control composition further comprises a surfactant. In some embodiments, the corrosion control composition further comprises a surfactant, biocide, and carrier.

In some embodiments, the surfactant is a nonionic, semi-nonionic, cationic, anionic, amphoteric, zwitterionic, gemini, dicationic, dianionic surfactant, or mixtures thereof. be.

In some embodiments, surfactants are alkylphenols, fatty acids, or mixtures thereof.

In some embodiments, the corrosion control composition further comprises an asphaltenic inhibitor, paraffin inhibitor, scale inhibitor, gas hydrate inhibitor, pH modifier, or any combination thereof.

In some embodiments, the corrosion control composition includes emulsion breakers, inverse emulsion breakers, coagulants/flocculants, water purification agents, dispersants, antioxidants, polymeric antidegradants, permeability control agents, foaming agents. agents, defoamers, emulsifiers, _CO2 and/or _O2 scavengers, gelling agents, lubricants, friction reducers, salts, or mixtures thereof.

In some embodiments, the corrosion control composition is a liquid, gel, or mixture comprising a liquid/gel and a solid.

In some embodiments, the corrosion control composition or its use solution is about 1 to about 11, about 1 to about 3, about 3 to about 5, about 5 to about 7, about 7 to about 9, about 9 to It has a pH of about 11, about 2, about 4, about 6, about 8, about 10, or any value therebetween.

In some embodiments, the corrosion control composition comprises from about 10% to about 80% by weight of the dicationic compound or mixtures thereof. In some other embodiments, the corrosion control composition comprises from about 10% to about 30%, from about 30% to about 50%, from about 50% to about 70%, from about 10% to about 40 wt%, about 20 wt% to about 50 wt%, about 30 wt% to about 60 wt%, about 40 wt% to about 80 wt%, about 15 wt%, about 25 wt%, about 35 wt%, about 45%, about 55%, about 65%, about 75%, or any value therebetween of dicationic compounds or mixtures thereof.

In some embodiments, the corrosion control composition comprises from about 20% to about 60% by weight of the dianionic compound or mixtures thereof. In some other embodiments, the corrosion control composition comprises from about 10% to about 30%, from about 30% to about 50%, from about 50% to about 70%, from about 10% to about 40 wt%, about 20 wt% to about 50 wt%, about 30 wt% to about 60 wt%, about 40 wt% to about 80 wt%, about 15 wt%, about 25 wt%, about 35 wt%, about 45%, about 55%, about 65%, about 75%, or any value therebetween of dianionic compounds or mixtures thereof.

In some embodiments, the dicationic or dianionic compound or mixture thereof has a concentration of about 1 ppm to about 1000 ppm in the treated water system. In some embodiments, the dicationic or dianionic compound or mixture thereof is about 1 ppm to about 5 ppm, about 5 ppm to about 10 ppm, about 1 ppm to about 10 ppm, about 1 ppm to about 20 ppm, about 1 ppm in the treated water system. to about 25 ppm, about 5 ppm to about 15 ppm, about 15 ppm to about 50 ppm, about 50 ppm to about 100 ppm, about 100 ppm to about 200 ppm, about 200 ppm to about 300 ppm, about 300 ppm to about 400 ppm, about 400 ppm to about 500 ppm, about 500 ppm to about 600 ppm, from about 600 ppm to about 700 ppm, from about 700 ppm to about 800 ppm, from about 800 ppm to about 900 ppm, or any value therebetween.

In some embodiments, the corrosion control composition is provided to the water system independently, simultaneously, or sequentially with the additional functional ingredients.

In some embodiments, the water system comprises fresh water, recycled water, salt water, surface water, produced water, or mixtures thereof. In some embodiments, aqueous systems include water, oil, and solids such as found in oil and gas operations. In some embodiments, the aqueous system comprises water and hydrocarbons or oils.

In some embodiments, water systems are used in cooling water systems, boiler water systems, oil wells, downhole formation, geothermal wells, mineral washing, flotation and charities, papermaking, gas scrubbers, air washers, continuous casting processes in the metallurgical industry, air conditioning and Refrigeration, water recycling, water purification, membrane filtration, food processing, clarifiers, municipal sewage treatment, municipal water treatment, or drinking water systems.

In some embodiments, the corrosion control composition or dicationic or dianionic compound disclosed herein is added to the treated water system after dosing the water system with the dicationic or dianionic compound or corrosion control composition. , from about 1 ppm to about 1,000 ppm, from about 1 ppm to about 900 ppm, from about 1 ppm to about 800 ppm, from about 1 ppm to about 700 ppm, from about 1 ppm to about 600 ppm, from about 1 ppm to about 500 ppm, from about 1 ppm to about 400 ppm, from about 1 ppm to about 300 ppm , about 1 ppm to about 250 ppm, about 1 ppm to about 200 ppm, about 1 ppm to about 150 ppm, about 1 ppm to about 100 ppm, about 1 ppm to about 50 ppm, about 1 ppm to about 25 ppm, about 1 ppm to about 10 ppm, about 0.5 ppm to about 2 ppm. , about 950 ppm, about 850 ppm, about 750 ppm, about 650 ppm, about 550 ppm, about 450 ppm, about 350, about 250 ppm, about 150 ppm, about 50 ppm, about 25 ppm, about 10 ppm, about 5 ppm, about 2 ppm, about 1 ppm, about 0.5 ppm , or any range or value therebetween, prevents corrosion on surfaces in aqueous systems, as demonstrated by the bubble cell test described in the Examples section of this disclosure. be able to.

The methods and compositions of the disclosure may comprise, consist essentially of, or consist of the components and components of the disclosed compositions or methods, as well as other components described herein. As used herein, “consisting essentially of” means that the methods and compositions may include additional steps, components, or ingredients, provided that the additional steps, components, or ingredients are It is meant only so long as it does not materially alter the basic and novel features of the claimed methods and compositions.

Alkalinity Source The disclosed method of preparation may comprise using an effective amount of an alkalinity source as a catalyst. The disclosed corrosion control compositions or methods of use thereof can also include using an effective amount of an alkalinity source. The alkalinity source can be added to the reaction mixture in its solid, liquid, or solution form.

Generally, an effective amount of alkalinity source should be considered as an amount that provides a plate mixture having a pH of at least about 8. When the solution has a pH of about 8 to about 10, it may be considered weakly alkaline, and when the pH is greater than about 12, the solution may be considered caustic.

Alkalinity sources can include alkali metal carbonates, alkali metal hydroxides, alkali metal silicates, or mixtures thereof. Suitable metal carbonates that can be used include, for example, sodium or potassium carbonate, bicarbonate, sesquicarbonate, or mixtures thereof. Suitable alkali metal hydroxides that can be used include, for example, sodium hydroxide, lithium hydroxide, or potassium hydroxide. Examples of useful alkali metal silicates include sodium or potassium silicates (having a M ₂ O:SiO ₂ ratio of 2.4 to 5:1, where M represents an alkali metal) or metasilicates is included. Metasilicates can be made by mixing hydroxides and silicates. The alkalinity source can also include metal borates such as sodium or potassium borate.

式中、Ｒは、長アルキル鎖を表し、Ｒ’、Ｒ’’、およびＲ’’’は、長アルキル鎖、またはより小さいアルキル基もしくはアリール基、あるいは水素のいずれかであってもよく、Ｘは、アニオンを表す。 Alkalinity sources can also include ethanolamines, urea sulfates, amines, amine salts, and quaternary ammoniums. The simplest cationic amines, amine salts and quaternary ammonium compounds are:

wherein R represents a long alkyl chain, R′, R″ and R′″ may be either long alkyl chains or smaller alkyl or aryl groups or hydrogen; X represents an anion.

In some embodiments, the method of preparation does not include an alkalinity source because the reactants contain primary amines or primary amine groups to catalyze the reaction.

Primary Alkalinity Source The disclosed compositions can include a primary alkalinity source, particularly when the disclosed composition is a detergent composition.

The primary alkalinity source of the compositions or detergent compositions disclosed herein comprises, for example, alkali metal hydroxides, alkali metal carbonates, alkali metal silicates, alkali metal metasilicates, or mixtures thereof be able to. Examples of suitable alkalinity sources include, but are not limited to, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium silicate, sodium metasilicate, potassium silicate, or mixtures thereof. The alkalinity source is preferably an alkali hydroxide, an alkali carbonate, or a mixture thereof. The alkalinity source controls the pH of the resulting use solution of the disclosed compositions when water or other diluent is added to the composition to form the use solution.

If the disclosed composition is a detergent composition, the pH of the use solution should be maintained in the alkaline range to provide adequate cleaning properties. Accordingly, the disclosed detergent compositions contain more primary alkalinity sources than the disclosed compounds disclosed herein in terms of weight percent.

A use solution of a composition disclosed herein, as used herein, refers to a diluted solution of a composition or compound in a diluent. Diluent, as used herein, refers to water, tap water, distilled water, or carrier solvent as defined herein. The composition or compound may be diluted 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 to 1,000,000 fold, or any value therebetween. to form a use solution, which can then be used for this application. In this disclosure, when a composition or a dicationic compound is applied, either the composition/compound or its use solution is applied.

When the disclosed composition is a detergent composition, the pH of the use solution of the detergent composition is from 0.1 g/L to about 3 g/L, where the use solution is obtained by diluting the detergent composition with distilled water. is defined as the pH determined at room temperature when containing a primary alkalinity source of In some embodiments, the concentration of the alkalinity source is from about 0.1 g/L to about 0.5 g/L, from about 0.5 g/L to about 1 g/L, from about 1 g/L to about 3 g in the use solution. /L, about 1 g/L to about 2 g/L, about 2 g/L to about 3 g/L, about 0.1 g/L, about 0.2 g/L, about 0.3 g/L, about 0.4 g/L , about 0.5 g/L, about 1.0 g/L, about 1.5 g/L, about 2.0 g/L, about 2.5 g/L, about 3.0 g/L, or any in between value.

Alternatively, if the disclosed composition is a detergent composition, the pH of the use solution of the detergent composition is obtained by diluting the detergent composition with distilled water, and the pH of the use solution is from 0.5 g/L to about 5 g. /L of the composition as determined at room temperature. In some embodiments, the concentration of the composition is about 0.5 g/L to about 1 g/L, about 1 g/L to about 2 g/L, about 2 g/L to about 3 g/L, about 3 g/L to about 4 g/L, about 4 g/L to about 5 g/L, about 0.5 g/L, about 1.0 g/L, about 1.5 g/L, about 2.0 g/L, about 2. 5 g/L, about 3.0 g/L, about 3.5 g/L, about 4.0 g/L, about 4.5 g/L, about 5.0 g/L, or any value therebetween.

Thus, in some embodiments, the detergent composition use solution has a primary alkalinity source of about 0.1 g/L, about 0.2 g/L, about 0.5 g/L, about 0.8 g/L, or at a concentration of about 1 gram per liter (g/L), a pH of at least about 8, preferably from about 9.5 to about 12, more preferably from about 10 to about 11 or from about 11 to about 12; offer. Thus, in some embodiments, the detergent composition use solution has a primary alkalinity source of about 1 g/L, about 1.5 g/L, about 2.0 g/L, about 2.5 g/L in distilled water. , about 3 g/L, or any value therebetween, provides a pH of at least 8, preferably 9.5 to 11, more preferably 10 to 11, about 11 to about 12 .

Accordingly, in some other embodiments, the use solution of the detergent composition comprises about 0.5 g/L, about 0.8 g/L, about 1 g/L, about 1.5 g/L, about 1.5 g/L of the composition itself. Concentration of 2.0 g/L, about 2.5 g/L, about 3.0 g/L, about 3.5 g/L, about 4.0 g/L, about 4.5 g/L, or about 5.0 g/L provides a pH of at least about 8, preferably from about 9.5 to about 12, more preferably from about 10 to about 11 or from about 11 to about 12. Thus, in some embodiments, the detergent composition use solution contains about 1 g/L, about 1.5 g/L, about 2.0 g/L, about 2.5 g/L, about 3 g of the composition itself. /L, about 3.5 g/L, about 4.0 g/L, about 4.5 g/L, about 5.0 g/L, or any value therebetween, at a pH of at least 8; Preferably a pH of 9.5-11, more preferably 10-11, about 11 to about 12 is provided.

In some embodiments, the pH of the use solution is from about 10 to about 13. In some embodiments, the pH of the use solution is about 8 to about 10. Specifically, the pH of the use solution is about 11-12. If the pH of the use solution is too low, eg, less than about 10, the use solution may not provide adequate cleaning properties. Additionally, at lower pH levels, silicate species can become unstable and precipitate out of solution. If the pH of the use solution is too high, eg, greater than about 13, the use solution is too alkaline and can attack or damage the surface being cleaned. A further consideration of pH is that if the composition is too alkaline, the user will need to wear PPE. However, if the pH of the composition is less than or equal to about 11.5 pH, no PPE is required. Therefore, the pH of the detergent compositions disclosed herein in dilute use form is desirably between about 11 and about 12 so that the composition is effective but not corrosive to human skin. .

Preferably, the primary alkalinity source is an alkali metal hydroxide. Preferred alkali metal hydroxides include sodium hydroxide and lithium hydroxide. More preferably, the primary alkalinity source is sodium hydroxide. Sodium carbonate may be light or heavy.

When carbonates are included in the disclosed detergent compositions, an effective amount of alkali metal carbonate has a pH of at least 8, preferably from 9.5 to 11, more preferably from 10 to 10.3. It is an amount that provides a solution.

Generally, when the primary alkalinity source is present in the disclosed detergent compositions at a concentration of at least about 1% by weight, the composition or use solution of the composition is capable of emulsifying fats and oils present. When the primary alkalinity source is present at a concentration of about 3% by weight or greater, the composition or use solution of the composition can emulsify, suspend, and separate fats and oils after processing.

In some embodiments where the disclosed composition is not a detergent composition, the composition does not contain a primary alkalinity source.

Acids Generally, acids, as used in this disclosure, include both organic and inorganic acids. Organic acids include, but are not limited to, hydroxyacetic acid (glycolic acid), formic acid, acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, gluconic acid, itaconic acid, trichloroacetic acid, urea hydrochloride, and benzoic acid. Not limited. Organic acids also include dicarboxylic acids such as oxalic acid, malonic acid, succinic acid, glutaric acid, maleic acid, fumaric acid, adipic acid, and terephthalic acid. Combinations of these organic acids may also be used. Inorganic acids include, but are not limited to, mineral acids such as phosphoric acid, sulfuric acid, sulfamic acid, methylsulfamic acid, hydrochloric acid, hydrobromic acid, hydrofluoric acid, and nitric acid. Inorganic acids can be used alone, in combination with other inorganic acid(s), or in combination with one or more organic acids. Acid generators, including, for example, potassium fluoride, sodium fluoride, lithium fluoride, ammonium fluoride, ammonium bifluoride, sodium silicofluoride, and the like, may be used to form suitable acids.

Examples of particularly suitable acids in the methods or compositions disclosed herein include inorganic acids and organic acids. Exemplary inorganic acids include phosphoric acid, phosphonic acid, sulfuric acid, sulfamic acid, methylsulfamic acid, hydrochloric acid, hydrobromic acid, hydrofluoric acid, and nitric acid. Exemplary organic acids include hydroxyacetic acid (glycolic acid), citric acid, lactic acid, formic acid, acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, gluconic acid, itaconic acid, trichloroacetic acid, urea hydrochloride, and benzoic acid. acid. Organic dicarboxylic acids such as oxalic acid, maleic acid, fumaric acid, adipic acid, and terephthalic acid can also be used.

Peroxycarboxylic Acids and Peroxycarboxylic Acid Compositions Peroxycarboxylic acids (ie, peracids) or peroxycarboxylic acid compositions can be included in the articles, products, or compositions disclosed herein. As used herein, the term "peracid" may also be referred to as "percarboxylic acid,""peroxycarboxylicacid," or "peroxyacid." Sulfoperoxycarboxylic acids, sulfonated peracids, and sulfonated peroxycarboxylic acids are also included within the terms "peroxycarboxylic acid" and "peracid" as used herein. As understood by those skilled in the art, a peracid refers to an acid in which the hydrogen of the hydroxyl group in the carboxylic acid is replaced with a hydroxy group. Oxidized peracids are sometimes referred to herein as peroxycarboxylic acids.

Peracids include any compound of the formula R--(COOOH) _n , where R is hydrogen, alkyl, alkenyl, alkyne, acyl, cycloaliphatic, aryl, heteroaryl, or heterocyclic and n is 1, 2, or 3, named by prefixing the parent acid with peroxy. Preferably R comprises hydrogen, alkyl or alkenyl. The terms "alkyl", "alkenyl", "alkyne", "acyl", "cycloaliphatic group", "aryl", "heteroaryl" and "heterocyclic group" are defined herein That's right.

A peroxycarboxylic acid composition, as used herein, refers to any composition comprising one or more peracids, their corresponding acids, and hydrogen peroxide or other oxidizing agents. Peroxycarboxylic acid compositions can also include stabilizers, fluorescently active tracers or compounds, or other ingredients, as known to those skilled in the art.

As used herein, the term "mixed" or "mixture" refers to a "percarboxylic acid composition," "percarboxylic acid," "peroxycarboxylic acid composition," or "peroxycarboxylic acid." refers to a composition or mixture comprising two or more percarboxylic or peroxycarboxylic acids. Peracids such as peracetic acid and peroctanoic acid may also be used. Any combination of these acids can also be used.

However, in some embodiments, the article, product, or composition does not contain a peroxycarboxylic acid or peroxycarboxylic acid composition.

Builders The detergent compositions disclosed herein comprise one or more builders. In some embodiments, builders can also function as part of the primary alkalinity source in the detergent composition. In some embodiments, builders include carbonates, hydroxides, metasilicates, or mixtures thereof. In some embodiments, carbonates can act as hydratable salts and thus can help provide a solid detergent composition.

Examples of suitable builders include, but are not limited to, alkali metal carbonates, alkali metal hydroxides, and alkali metal silicates. Exemplary alkali metal carbonates that may be used include, but are not limited to, carbonate, bicarbonate, sodium or potassium sesquicarbonate, and mixtures thereof. Exemplary alkali metal hydroxides that may be used include, but are not limited to, sodium hydroxide or potassium hydroxide. Alkali metal hydroxides can be added to the composition in any form known in the art, including solid beads, dissolved in an aqueous solution, or combinations thereof. Examples of alkali metal silicates include, but are not limited to, sodium or potassium silicic acid or polysilicates, sodium or potassium metasilicate, and sodium or potassium metasilicate hydrates, or combinations thereof.

In some embodiments, the composition does not contain a builder.

Chelating Agents The detergent compositions disclosed herein may also contain a chelating agent. Chelating agents include, but are not limited to, chelating agents (chelators), sequestering agents (sequestrants), detergent builders, and the like. Examples of chelating agents include phosphonates, phosphates, aminocarboxylates and their derivatives, pyrophosphates, polyphosphates, ethylenediamine and ethylenetriamine derivatives, hydroxy acids, and mono-, di-, and tri- - carboxylates, as well as their corresponding acids, but are not limited to these. Other exemplary chelating agents include aluminosilicates, nitroloacetates and derivatives thereof, and mixtures thereof.

Suitable aminocarboxylic acids according to the present invention include methylglycinediacetic acid (MGDA), glutamic-N,N-diacetic acid (GLDA), N-hydroxyethylaminodiacetic acid, ethylenediaminetetraacetic acid (EDTA) (tetrasodium EDTA ), hydroxyethylenediaminetetraacetic acid, diethylenetriaminepentaacetic acid, N-hydroxyethyl-ethylenediaminetriacetic acid (HEDTA), diethylenetriaminepentaacetic acid (DTPA), ethylenediaminesuccinic acid (EDDS), 2-hydroxyethyliminodiacetic acid (HEIDA), include, but are not limited to, iminodisuccinic acid (IDS), 3-hydroxy-2-2'-iminodisuccinic acid (HIDS), and other similar acids or salts thereof having amino groups with carboxylic acid substituents. . Additional descriptions of suitable aminocarboxylates suitable for use as chelating agents and/or sequestering agents can be found in Kirk-Othmer, Encyclopedia of Chemical Technology, Third Edition, volume 5, pages 339-366 and volume 23, pages 319-320, the disclosure of which is incorporated herein by reference.

Chelating agents may be water soluble and/or biodegradable. Other exemplary chelating agents include TKPP (tetrapotassium pyrophosphate), PAA (polyacrylic acid) and its salts, phosphonobutanecarboxylic acid, alanine, N,N-bis(carboxymethyl)-, trisodium salt. , and sodium gluconate.

In some embodiments, the chelating agent is phosphorus free. In some embodiments, chelating agents can also function as solidifying agents to help form solid compositions, such as the sodium salt of citric acid.

Preferably, the chelating agent is the sodium salt of an aminocarboxylate. More preferably, the chelating agent is methylglycinediacetic acid (MGDA). Synergistic water conditioning is achieved using methylglycine diacetic acid (MGDA) in combination with polyacrylic acid and its salts.

In some embodiments, the compositions disclosed herein are free of chelating agents, detergent builders, or both. In some embodiments, the compositions disclosed herein are free of phosphorus-containing chelating agents, detergent builders, or both.

Scale Inhibitor The inverse emulsion breaking composition can further comprise a scale inhibitor. Suitable scale inhibitors include phosphates, phosphate esters, phosphoric acid, phosphonates, phosphonic acids, polyacrylamides, salts of Sacrylamidomethyl propanesulfonate/acrylic acid copolymer (AMPS/AA), Phosphorylated maleic acid copolymers (PHOS/MA), mono-, bis-, and oligomeric phosphinosuccinic acid (PSO) derivatives, polycarboxylic acids, hydrophobically modified polycarboxylic acids, and polymaleic acid/acrylic acid/acrylamidomethylpropanesulfonate terpolymers Examples include but are not limited to salts of (PMA/AA/AMPS).

In some embodiments, the compositions disclosed herein do not contain scale inhibitors.

Enzymes The compositions or detergent compositions disclosed herein may comprise enzymes. Enzymes in the detergent compositions enhance soil removal, prevent redeposition, and/or reduce suds during application of the detergent compositions or their use solutions. The function of enzymes is to break down sticky soils such as starches or proteinaceous materials typically found on soiled surfaces and removed by the detergent composition into the wash water source.

Exemplary types of enzymes that may be incorporated into the detergent compositions disclosed herein include amylase, protease, lipase, cellulase, cutinase, gluconase, peroxidase, and/or mixtures thereof. Not limited. The compositions disclosed herein may employ two or more enzymes from any suitable source, such as plant, animal, bacterial, fungal, or yeast sources. In some embodiments the enzyme is a protease. As used herein, the term "protease" or "proteinase" refers to an enzyme that catalyzes the hydrolysis of peptide bonds.

As one skilled in the art will recognize, enzymes are designed to work on specific types of soils. For example, according to one embodiment of the present invention, in warewashing applications, protease enzymes are used because they are effective in high temperature warewashers and effective in reducing protein-based soils. good too. Protease enzymes are particularly useful for cleaning protein-containing soils such as blood, skin dander, mucus, grass, food (eg, eggs, milk, spinach, meat residue, tomato sauce). Protease enzymes are capable of cleaving macromolecular protein linkages of amino acid residues, converting substrates into small fragments that are readily soluble or dispersible in aqueous solutions of use. Proteases are often referred to as detersive enzymes because of their ability to break down soil through a chemical reaction known as hydrolysis. Protease enzymes can be obtained, for example, from Bacillus subtilis, Bacillus licheniformis and Streptomyces griseus. Protease enzymes are also commercially available as serine endoproteases.

Examples of commercially available protease enzymes are available under the following trade names: Esperase, Purafect, Purafect L, Purafect Ox, Everlase, Liquanase, Savinase, Prime L, Prosperase and Blap.

Enzymes included in the detergent composition may be separate entities and/or may be formulated in combination with the detergent composition. In some embodiments, enzymes may be incorporated into detergent compositions in either liquid or solid formulations. Additionally, enzymes may be formulated in a variety of delayed or controlled release formulations. For example, solid cast detergent compositions can be prepared without the application of heat. As those skilled in the art will appreciate, enzymes tend to be denatured by the application of heat, and thus the use of enzymes within detergent compositions, as a step in the forming process, such as solidification, is a non-heat dependent detergent composition. What is needed is a way to form

Enzymes may also be commercially available in solid (ie, packs, powders, etc.) or liquid formulations. Commercially available enzymes are commonly combined with stabilizers, buffers, cofactors, and inert media. The actual active enzyme content depends on the method of manufacture, which is well known to those skilled in the art, and such method of manufacture is not critical to the present invention.

Alternatively, the enzyme composition may be provided separately from the detergent composition, such as being added directly to the detergent composition or cleaning liquor use solution or application, eg, dishwasher wash water.

Other Additional Detergent Composition Agents The detergent compositions disclosed herein may comprise one or more additional detergent composition agents. Exemplary additional detergent composition agents include anti-ionic deposition agents; crystal modifiers; hardeners; bleaching agents; peroxycarboxylic acids, peroxycarboxylic acid compositions, fillers; Dispersing agents; fragrances and dyes; and thickening agents, but are not limited to.

In some embodiments, the detergent compositions disclosed herein do not contain one, more, or all additional detergent composition agents.

Additional Corrosion Control Composition Agents in the Corrosion Control Composition In addition to the one or more dicationic, dianionic compounds derived from primary amines described herein, the corrosion control composition of the present disclosure contains one and additional corrosion control composition agents as described above.

Additional corrosion control composition agents in the disclosed corrosion control compositions include carriers, acids, dispersants, biocides, additional corrosion inhibitors, fouling control agents, antioxidants, polymeric antidegradants, penetrants, nature modifiers, blowing agents, defoamers, crushed proppants, _H2S , _CO2 , and/or _O2 scavengers, gelling agents, lubricants, and friction modifiers, salts, or mixtures thereof. can be, but are not limited to:

Additional corrosion control composition agents in the disclosed corrosion control compositions also include organic sulfur compounds, asphaltenes inhibitors, paraffin inhibitors, scale inhibitors, water purification agents, emulsion breakers, inverse emulsion breakers, gas It may include, but is not limited to, hydrate inhibitors, pH modifiers, surfactants, or any combination thereof.

Additionally, additional corrosion control composition agents may include sequestering agents, solubilizers, lubricants, buffers, detergents, rinse aids, preservatives, binders, thickeners or other viscosity modifiers, processing agents. Auxiliaries, carriers, water conditioners, or foam generators, anti-ionic agents or systems, aesthetic improvers (e.g., dyes, odorants, perfumes), or other additives suitable for combination with inverse emulsion breaking agents. agents, or mixtures thereof.

Additional corrosion control composition agents in the corrosion control compositions disclosed herein will vary according to the particular corrosion control composition being manufactured and its intended use, as will be appreciated by those skilled in the art.

Alternatively, the corrosion control composition does not contain or contain one or more of the additional corrosion control composition agents.

When one or more additional corrosion control composition agents are used in the corrosion control composition disclosed herein, they may be added to the same corrosion control composition with the dicationic or dianionic agents described herein. can be formulated together with the compound. Alternatively, some or all of the additional corrosion control composition agents may be formulated in one or more different formulations and delivered to the water system or surface. In other words, the additional corrosion control composition agents can be provided independently, simultaneously, or sequentially in the water system or on the surface.

Biocide and Carrier In some embodiments, the corrosion control compositions disclosed herein further comprise a biocide in addition to the dicationic or dianionic compound. In some other embodiments, the corrosion control compositions disclosed herein further comprise a carrier. In some other embodiments, corrosion control compositions disclosed herein further comprise a biocide and a carrier. In some embodiments, the methods or corrosion control compositions disclosed herein can consist of one or more dicationic or dianionic compounds disclosed herein and a carrier. In some embodiments, the corrosion control compositions disclosed herein consist of one or more dicationic or dianionic compounds disclosed herein, a carrier, and a biocide.

Biocides suitable for use may be oxidizing or non-oxidizing biocides. Oxidizing biocides include, but are not limited to, bleach, chlorine, bromine, chlorine dioxide, and materials capable of releasing chlorine and bromine. Non-oxidizing biocides include glutaraldehyde, isothiazoline, 2,2-dibromo-3-nitrilopropionamide, 2-bromo-2-nitropropane-1,3diol, 1-bromo-1-(bromomethyl)-1 , 3-propanedicarbonitrile, tetrachloroisophthalonitrile, alkyldimethylbenzylammonium chloride, dimethyldialkylammonium chloride, didecyldimethylammonium chloride, poly(oxyethylene(dimethyliminio)ethylene(dimethyliminio)ethylene dichloride, methylene Bisthiocyanate, 2-decylthioethanamine, tetrakishydroxymethylphosphonium sulfate, dithiocarbamate, cyanodithioimidocarbonate, 2-methyl-5-nitroimidazole-1-ethanol, 2-(2-bromo-2-nitroethenyl)furan , β-bromo-β-nitrostyrene, β-nitrostyrene, β-nitrovinylfuran, 2-bromo-2-bromomethylglutaronitrile, bis(trichloromethyl)sulfone, S-(2-hydroxypropyl)thiomethane sulfonate, tetrahydro-3,5-dimethyl-2H-1,3,5-hydrazine-2-thione, 2-(thiocyanomethylthio)benzothiazole, 2-bromo-4′-hydroxyacetophenone, 1,4-bis( Bromoacetoxy)-2-butene, bis(tributyltin) oxide, 2-(tert-butylamino)-4-chloro-6-(ethylamino)-s-triazine, dodecylguanidine acetate, dodecylguanidine hydrochloride, cocoalkyldimethyl Amine oxide, n-cocoalkyltrimethylenediamine, tetra-alkylphosphonium chloride, 7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid, 4,5-dichloro-2-n-octyl-4 -isothiazolin-3-one, 5-chloro-2-methyl-4-isothiazolin-3-one, and 2-methyl-4-isothiazolin-3-one.

Suitable non-oxidizing biocides also include, for example, aldehydes (such as formaldehyde, glutaraldehyde, and acrolein), amine-type compounds (such as quaternary amine compounds and cocodiamine), halogenated compounds (such as 2-bromo- 2-nitropropane-3-diol (Bronopol) and 2-2-dibromo-3-nitrilopropionamide (DBNPA)), sulfur compounds (such as isothiazolones, carbamates, and metronidazole), and quaternary phosphonium salts (such as tetrakis (Hydroxymethyl)-phosphonium sulfate (THPS)).

Suitable oxidizing biocides include, for example, sodium hypochlorite, trichloroisocyanuric acid, dichloroisocyanuric acid, calcium hypochlorite, lithium hypochlorite, chlorinated hydantoins, stabilized sodium hypobromite, active Sodium bromide, brominated hydantoins, chlorine dioxide, ozone, peroxycarbons, peroxycarboxylic compositions, and peroxides.

The corrosion control composition is about 0.1 wt% to about 10 wt%, about 0.5 wt% to about 5 wt%, or about 0.5 wt% to about 4 wt% based on the total weight of the composition. of biocides. In some embodiments, the corrosion control composition does not contain a biocide. In some embodiments, the corrosion control composition does not contain an oxidizing biocide. In some other embodiments, the corrosion control composition is free of non-oxidizing biocides.

The carrier in the disclosed corrosion control compositions can be water, organic solvents, or a combination of water and organic solvents. Organic solvents can be alcohols, hydrocarbons, ketones, ethers, alkylene glycols, glycol ethers, amides, nitriles, sulfoxides, esters, or combinations thereof. Examples of suitable organic solvents include methanol, ethanol, propanol, isopropanol, butanol, 2-ethylhexanol, hexanol, octanol, decanol, 2-butoxyethanol, methylene glycol, ethylene glycol, 1,2-propylene glycol, 1,2-propylene glycol, 3-propylene glycol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, ethylene glycol monobutyl ether, ethylene glycol dibutyl ether, pentane, hexane, cyclohexane, methylcyclohexane, heptane, decane, dodecane, diesel, toluene, xylene, heavy aromatic naphtha, Examples include, but are not limited to, cyclohexanone, diisobutyl ketone, diethyl ether, propylene carbonate, N-methylpyrrolidinone, N,N-dimethylformamide, or combinations thereof.

The corrosion control composition comprises about 1 wt% to about 80 wt%, about 1 wt% to about 70 wt%, about 1 wt% to about 60 wt%, about 1 wt% to about 50% by weight, from about 1% to about 40%, from about 1% to about 30%, from about 1% to about 20%, from about 1% to about 10%, from about 5% to about 10 wt%, about 5 wt% to about 20 wt%, about 5 wt% to about 30 wt%, about 5 wt% to about 40 wt%, about 5 wt% to about 50 wt%, about 10 wt% to about 20 wt%, about 10 wt% to about 30 wt%, about 10 to about 40 wt%, about 10 wt% to about 50 wt%, about 10 wt%, about 20 wt%, about 30 wt%, about 40% , about 50%, about 60%, about 70%, about 80%, about 90%, or any value therebetween.

Anionic Surfactants Anionic surfactants are surface-active substances in which the charge of the hydrophobe is negative or in which the hydrophobic segment of the molecule carries a charge unless the pH is raised above neutrality (e.g. carboxylic acids). It is a surfactant that does not Carboxylates, sulfonates, sulfates and phosphates are polar (hydrophilic) solubilizing groups found in anionic surfactants. Of the cations (counterions) associated with these polar groups, sodium, lithium, and potassium confer water solubility, ammonium and substituted ammonium ions provide both water and oil solubility, calcium, barium , and magnesium promote oil solubility. As will be appreciated by those skilled in the art, anionic surfactants are excellent detersive surfactants and are therefore preferred additions to heavy duty detergent compositions.

Anionic sulfate surfactants suitable for use in the present compositions include _{alkyl ether sulfates, alkyl sulfates,} linear and branched primary and secondary alkyl sulfates, alkyl ethoxy sulfates, fatty oleyl glycerol sulfates. alkyl phosphates, alkylphenol ethylene oxide ether sulfates, C ₅ -C 17 acyl-N-(C 1 -C ₄ alkyl) and -N-(C ₁ -C ₂ hydroxyalkyl) glucamine sulfates, and alkyl polyglucoside sulfates Sulfates of polysaccharides and the like can be mentioned. Also, alkyl sulfates, alkylpoly(ethyleneoxy)ether sulfates, and aromatic poly(ethylene Oxy) sulfates are also included.

Suitable anionic sulfonate surfactants for use in the present compositions also include alkyl sulfonates, linear and branched primary and secondary alkyl sulfonates, and aromatic sulfonates with or without substituents. mentioned.

Anionic carboxylate surfactants suitable for use in the present compositions include carboxylic acids (and salts) such as alkanoic acids (and alkanoates), ester carboxylic acids (e.g. alkyl succinic acids), ether carboxylic acids, sulfonated and sulfonated fatty acids such as oleic acid. Such carboxylates include alkylethoxycarboxylates, alkylarylethoxycarboxylates, alkylpolyethoxypolycarboxylate surfactants, and soaps (eg, alkylcarboxyls). Secondary carboxylates useful in the present compositions include those containing a carboxyl unit attached to a secondary carbon. A secondary carbon can be in a ring structure, for example, as in p-octylbenzoic acid or in an alkyl-substituted cyclohexyl carboxylate. Secondary carboxylate surfactants typically do not contain ether linkages, ester linkages, and hydroxyl groups. Furthermore, they typically lack a nitrogen atom within the group-to-group (amphiphilic moieties). Suitable secondary soap surfactants generally contain 11 to 13 total carbon atoms, although more carbon atoms (eg, up to 16) may be present. Suitable carboxylates also include acylgluamates, acylpeptides, sarcosinates (e.g. N-acylsarcosinates), taurates (e.g. N-acyl taurates, and fatty acid amides of methyl tauride). and acyl amino acids (and salts) such as

であり、式中、Ｒ^１は、Ｃ_４～Ｃ_１６アルキル基であり、ｎは、１～２０の整数であり、ｍは、１～３の整数であり、Ｘは、水素、ナトリウム、カリウム、リチウム、アンモニウムなどの対イオンか、またはモノエタノールアミン、ジエタノールアミン、もしくはトリエタノールアミンなどのアミン塩である。いくつかの実施形態では、ｎは、４～１０の整数であり、ｍは、１である。いくつかの実施形態では、Ｒは、Ｃ_８～Ｃ_１６アルキル基である。いくつかの実施形態では、Ｒは、Ｃ_１２～Ｃ_１４アルキル基であり、ｎは、４であり、ｍは、１である。 Suitable anionic surfactants have the formula:
R—O—(CH ₂ CH2O) _n (CH ₂ ) _m —CO ₂ X(3)
alkyl or alkylaryl ethoxy carboxylates, wherein R is a C ₈ -C ₂₂ alkyl group or

wherein R ¹ is a C ₄ -C ₁₆ alkyl group, n is an integer from 1 to 20, m is an integer from 1 to 3, X is hydrogen, sodium, potassium , lithium, ammonium, or an amine salt such as monoethanolamine, diethanolamine, or triethanolamine. In some embodiments, n is an integer from 4-10 and m is 1. _In some embodiments, R is a C8 _- C16 alkyl group. In some embodiments, R is a C ₁₂ -C ₁₄ alkyl group, n is 4 and m is 1.

であり、Ｒ^１は、Ｃ_６～Ｃ_１２アルキル基である。さらにまた他の実施形態では、Ｒ^１は、Ｃ_９アルキル基であり、ｎは、１０であり、ｍは、１である。 In other embodiments, R is

and R ¹ is a C ₆ -C ₁₂ alkyl group. In still other embodiments, R ¹ is a C ₉ alkyl group, n is 10 and m is 1.

Such alkyl and alkylaryl ethoxy carboxylates are commercially available. These ethoxycarboxylates are typically available in the acid form and they can be readily converted to the anionic or salt form. Commercially available carboxylates include Neodox 23-4, C _12-13 alkyl polyethoxy(4) carboxylic acid (Shell Chemical), and Emcol CNP-110, C ₉ alkylaryl polyethoxy(10) carboxylic acid (Witco Chemical). are mentioned. Carboxylates are also available from Clariant, for example the product ^Sandopan® DTC, a C13 alkyl polyethoxy ₍ 7) carboxylic acid.

In some embodiments, the compositions or detergent compositions disclosed herein are free of anionic surfactants.

Nonionic Surfactants Useful nonionic surfactants are generally characterized by the presence of organic hydrophobic groups and organic hydrophilic groups, and are typically organic aliphatic, alkylaromatic, or polyoxyalkylene hydrophobic groups. It is produced by condensation of a polar compound with a hydrophilic alkaline oxide moiety, generally ethylene oxide or its polyhydration product, polyethylene glycol. Specifically, any hydrophobic compound having a hydroxyl, carboxyl, amino, or amido group with a reactive hydrogen atom may be added to ethylene oxide, or its polyhydration additives, or mixtures thereof with alkoxylenes such as propylene oxide. to form a nonionic surfactant. The length of the hydrophilic polyoxyalkylene moiety that condenses with any particular hydrophobic compound is such that it produces a water-dispersible or water-soluble compound with the desired degree of balance between hydrophilic and hydrophobic properties. , can be easily adjusted. Useful nonionic surfactants include

Block polyoxypropylene-polyoxyethylene polymer compounds based on propylene glycol, ethylene glycol, glycerol, trimethylolpropane, and ethylenediamine as initiator reactive hydrogen compounds. Examples of polymeric compounds made from sequential propoxylation and ethoxylation of an initiator are available from BASF Corp. It is commercially available from One class of compounds are bifunctional (two reactive hydrogen) compounds formed by condensing ethylene oxide with a hydrophobic base formed by the addition of propylene oxide to the two hydroxyl groups of propylene glycol. is. This hydrophobic portion of the molecule has a molecular weight of about 1,000 to about 4,000. Ethylene oxide is then added to sandwich this hydrophobe between the hydrophilic groups, controlled by length to constitute from about 10% to about 80% by weight of the final molecule. Another class of compounds are trifunctional block copolymers resulting from the sequential addition of propylene oxide and ethylene oxide to ethylenediamine. The molecular weight of the propylene oxide hydrotype ranges from about 500 to about 7,000; the hydrophilic ethylene oxide is added to make up about 10% to about 80% by weight of the molecule.

Condensation of 1 mole of an alkylphenol having a linear or branched configuration, or in which the alkyl chain of single or double alkyl constituents contains from about 8 to about 18 carbon atoms, and from about 3 to about 50 moles of ethylene oxide. product. Alkyl groups can be represented by, for example, diisobutylene, di-amyl, polymerized propylene, iso-octyl, nonyl, and di-nonyl. These surfactants may be polyethylene, polypropylene, and polybutylene oxide condensates of alkylphenols. Examples of commercial compounds of this chemistry are marketed under the trade names Igepal® from Rhone-Poulenc and Triton® from Union Carbide.

Condensation products of 1 mole of saturated or unsaturated straight or branched chain alcohols having from about 6 to about 24 carbon atoms and from about 3 to about 50 moles of ethylene oxide. The alcohol portion may consist of a mixture of alcohols within the carbon ranges described above, or may consist of alcohols having a specified number of carbon atoms within this range. Examples of similar commercial surfactants are Lutensol™, Dehydol™ from BASF, Shell Chemical Co.; Neodol™ from Vista Chemical Co.; It is available under the trade name Alfonic.TM.

Condensation products of 1 mole of saturated or unsaturated straight or branched chain carboxylic acids having from about 8 to about 18 carbon atoms and from about 6 to about 50 moles of ethylene oxide. The acid moiety may consist of a mixture of acids within the carbon atom ranges defined above, or may consist of acids having a specified number of carbon atoms within this range. Examples of commercial compounds of this chemistry are Disponil or Agnique from BASF and Lipo Chemicals, Inc.; It is commercially available under the trade name Lipopeg.TM.

In addition to ethoxylated carboxylic acids, commonly referred to as polyethylene glycol esters, other alkanoic acid esters formed by reaction with glycerides, glycerin, and polyhydric (saccharides or sorbitan/sorbitol) alcohols are specialized embodiments, It has particular application herein for indirect food additive applications. All of these ester moieties have one or more reactive hydrogen sites on their molecule that can be subjected to further acylation or ethylene oxide (alkoxide) addition to control the hydrophilicity of these materials. Care must be taken when adding these fatty esters or acylated carbohydrates to compositions of the invention containing amylase and/or lipase enzymes due to potential incompatibilities.

An example of a non-ionic low foaming surfactant is adding ethylene oxide to ethylene glycol to provide a hydrophile of the specified molecular weight, then adding propylene oxide to give modified by obtaining a hydrophobic block in , including but not limited to compounds that are essentially inverted. The hydrophobic portion of the molecule has a molecular weight of about 1,000 to about 3,100, and the central hydrophilic material comprises 10% to about 80% by weight of the final molecule. These reversed Pluronics™ are manufactured by BASF Corporation under the trademark Pluronic™ R surfactants. Similarly, Tetronic™ R surfactants are manufactured by BASF Corporation by the sequential addition of ethylene oxide and propylene oxide to ethylene diamine. The hydrophobic portion of the molecule has a molecular weight of about 2,100 to about 6,700, and the central hydrophilic material comprises 10% to about 80% by weight of the final molecule.

To reduce foaming due to reaction with small hydrophobic molecules such as propylene oxide, butylene oxide, benzyl chloride, and short chain fatty acids, alcohols, or alkyl halides containing 1-5 carbon atoms, and mixtures thereof , modified by "capping" or "endblocking" the terminal hydroxy group(s) (of the multifunctional moiety). Also included are reactants such as thionyl chloride that convert terminal hydroxy groups to chloride groups. Such modifications to terminal hydroxy groups can result in all-block, block-heteric, heteric-block, or all-heteric nonionics.

式中、Ｒは、８～９個の炭素原子のアルキル基であり、Ａは、３～４個の炭素原子のアルキレン鎖であり、ｎは、７～１６の整数であり、ｍは、１～１０の整数である。 Additional examples of effective low-foaming nonionic surfactants are described in Brown et al. The alkylphenoxypolyethoxyalkanols of U.S. Pat. No. 2,903,486 issued to, but not limited to, represented by the formula:

wherein R is an alkyl group of 8-9 carbon atoms, A is an alkylene chain of 3-4 carbon atoms, n is an integer of 7-16, m is 1 An integer from ˜10.

Having alternating hydrophilic oxyethylene chains and hydrophobic oxypropylene chains in which the weight of the terminal hydrophobic chains, the weight of the intermediate hydrophobic units, and the weight of the linking hydrophilic units each represent about one-third of the condensate , August 7, 1962 Martin et al. The polyalkylene glycol condensates of U.S. Pat. No. 3,048,548 issued to U.S. Pat.

Z is an alkoxylatable material, R is a radical derived from an alkylene oxide, which can be ethylene and propylene, n is an integer from, for example, 10 to 2,000 or more, and z is the reaction U.S. Pat. No. 3,382, issued May 7, 1968 to Lissant et al., having the general formula Z[(OR) _nOH ] _z , an integer determined by the number of oxyalkylatable groups. , 178, and antifoaming nonionic surfactants.
Y is the residue of an organic compound having about 1-6 carbon atoms and one reactive hydrogen atom, n has an average value of at least about 6.4 as determined by the hydroxyl number; _m corresponds to the formula Y( _C3H6O ) _{n ( C2H4O} ) _mH with a value such that the oxyethylene moiety constitutes from about 10% to about 90% by weight of the molecule; Conjugated polyoxyalkylene compounds as described in US Pat. No. 2,677,700, issued May 4, 1954 to Jackson et al.

No. _2,674,619 , issued April ₆ , 1954 to Lundsted et al., having the formula Y[( _{C3H6On ( C2H4O} ) _mH ] _x wherein Y has about 2 to 6 carbon atoms and contains x reactive hydrogen atoms, where x has a value of at least about 2. is the residue of the compound, n has a value such that the polyoxypropylene hydrophobic base has a molecular weight of at least about 900, and m has a molecular weight of about 10% to about 90% by weight. Compounds that fall within the definition for Y include, for example, propylene glycol, glycerin, pentaerythritol, trimethylolpropane, ethylenediamine, etc. The oxypropylene chain is optional, although , beneficially contains a small amount of ethylene oxide, and the oxyethylene chain optionally also beneficially contains a small amount of propylene oxide.

Additional conjugated polyoxyalkylene surfactants advantageously used in the compositions of the present invention correspond to the formula: P[( _C3H6O ) _{n ( C2H4O ) mH} ] _x and have the formula wherein P is the residue of an organic compound having about 8 to 18 carbon atoms and containing x reactive hydrogen atoms, x has a value of or 2, and n is the polyoxyethylene moiety It has a value such that the molecular weight is at least about 44 and m has a value such that the oxypropylene content of the molecule is from about 10% to about 90% by weight. In either case, the oxypropylene chains may optionally but advantageously contain a small amount of ethylene oxide, and the oxyethylene chains also optionally but advantageously contain a small amount of propylene oxide. may

Polyhydroxy fatty acid amide surfactants suitable for use in the present compositions have the structural formula R ₂ CON _R1 Z, where R1 is H, C ₁ -C ₄ hydrocarbyl, 2-hydroxyethyl, 2-hydroxypropyl, ethoxy, propoxy groups, or mixtures thereof; R ₂ is a C ₅ -C ₃₁ hydrocarbyl which may be linear; Z is a linear hydrocarbyl chain having at least three hydroxyls directly attached to the chain or alkoxylated derivatives thereof (preferably ethoxylated or propoxylated). Z can be derived from a reducing sugar in a reductive amination reaction, such as a glycityl moiety.

Alkyl ethoxylate condensation products of fatty alcohols with from about 0 to about 25 moles of ethylene oxide are suitable for use in the present compositions. The alkyl chains of fatty alcohols can be straight or branched, primary or secondary, and generally contain from 6 to 22 carbon atoms.

Ethoxylated C ₆ -C ₁₈ fatty alcohols and C ₆ -C ₁₈ mixed ethoxylated and propoxylated fatty alcohols, especially those that are water-soluble, are suitable surfactants for use in the present compositions. Suitable ethoxylated fatty alcohols include C ₆ -C ₁₈ ethoxylated fatty alcohols having a degree of ethoxylation of 3-50.

Nonionic alkyl polysaccharide surfactants particularly suitable for use in the present compositions include those disclosed in US Pat. No. 4,565,647, Llenado, issued Jan. 21, 1986. US Pat. These surfactants contain a hydrophobic group containing from about 6 to about 30 carbon atoms and a polysaccharide, eg, a polyglycoside, a hydrophilic group containing from about 1.3 to about 10 saccharide units. Any reducing saccharide containing 5 or 6 carbon atoms can be used, eg, glucose, galactose, and galactosyl moieties can be replaced with glucosyl moieties. (Optionally, hydrophobic groups are attached at the 2-, 3-, 4-, etc. positions, thus producing glucose or galactose, as opposed to glucosides or galactosides.) Linkages between saccharides, for example, additional and the 2-, 3-, 4-, and/or 6-position on the preceding saccharide unit.

Fatty acid amide surfactants suitable for use in the present compositions include those having the formula: _R6CON ( _R7 ) ₂ , wherein R6 is an alkyl group containing from ₇ to 21 carbon atoms. , each R ₇ is independently hydrogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ hydroxyalkyl, or --(C ₂ H ₄ O) _X H, and x is in the range of 1 to 3 be.

A useful class of nonionic surfactants includes those defined as alkoxylated amines or, most specifically, alcohol alkoxylated/aminated/alkoxylated surfactants. These nonionic surfactants, at least in part, have the general formula: R ²⁰ --(PO) _S N--(EO) _t H, R ²⁰ --(PO) _S N--(EO) _t H(EO) _t H, and R ²⁰ —N(EO) _t H, wherein R ²⁰ is an alkyl, alkenyl or other aliphatic group, or 8 to 20, preferably 12 to 14 an alkyl-aryl group of 1 carbon atom, EO is oxyethylene, PO is oxypropylene, s is 1 to 20, preferably 2 to 5, t is 1 to 10, preferably 2 ∼5 and u is 1-10, preferably 2-5. Other variations in the scope of these compounds may be represented by the alternative formula: R ²⁰ --(PO) _V --N[(EO) _w H][(EO) _z H], where R ²⁰ is as defined above, v is 1 to 20 (e.g. 1, 2, 3, or 4 (preferably 2)), and w and z are independently 1 to 10, preferably 2-5. These compounds are commercially represented by the product line marketed by Huntsman Chemicals as nonionic surfactants. A preferred chemical of this class includes Surfonic™ PEA25 amine alkoxylate. Preferred nonionic surfactants for compositions of the present invention include alcohol alkoxylates, EO/PO block copolymers, alkylphenol alkoxylates, and the like.

Article, Nonionic Surfactants, edited by Schick, M.; J. , Vol. 1 of the Surfactant Science Series, Marcel Dekker, Inc.; , New York, 1983 is an excellent reference on a wide variety of nonionic compounds commonly used in the practice of this invention. A representative list of the nonionic class and these surfactant species is described in US Pat. No. 3,929,678, issued Dec. 30, 1975 to Laughlin and Heuring. Further examples are described in "Surface Active Agents and detergents" (Volumes I and II, Schwartz, Perry and Berch).

Nonionic surfactants suitable for use with the compositions of the present invention include alkoxylated surfactants. Suitable alkoxylated surfactants include EO/PO copolymers, fully terminated or partially terminated EO/PO copolymers, alcohol alkoxylates, terminated alcohol alkoxylates, mixtures thereof, and the like. Alkoxylated surfactants suitable for use as solvents include EO/PO block copolymers such as Pluronic and inverse Pluronic surfactants, alcohol alkoxylates such as Dehypon LS-54 (R-(EO) ₅ (PO ) ₄ ) and Dehypon LS-36 (R—(EO) ₃ (PO) ₆ ), and terminated alcohol alkoxylates such as Plurafac LF221 and Tegoten EC11, mixtures thereof, and the like.

In some embodiments that are not detergent compositions, the compositions disclosed herein are free of nonionic surfactants.

Semipolar Nonionic or Semi-Nonionic Surfactants Semipolar types of nonionic surfactants are another class of nonionic surfactants useful in the compositions disclosed herein. In general, semi-polar nonionic (semi-nonionic) surfactants are high foaming agents and foam stabilizers, which can limit their application in CIP systems. However, in some embodiments designed for high foaming compositions or detergent compositions, semi-polar nonionic surfactants are of immediate utility. Semi-polar nonionic surfactants include, but are not limited to, amine oxides, phosphine oxides, sulfoxides, and their alkoxylated derivatives.

式中、矢印は、半極性結合の従来の表示であり、Ｒ^１、Ｒ^２、およびＲ^３は、脂肪族、芳香族、複素環式、脂環式、またはそれらの組み合わせであり得る。一般に、対象となる洗剤のアミンオキシドに関して、Ｒ^１は、約８～約２４個の炭素原子のアルキルラジカルであり、Ｒ^２およびＲ^３は、１～３個の炭素原子のアルキルもしくはヒドロキシアルキル、またはそれらの混合物であり、Ｒ^２およびＲ^３は、例えば、酸素もしくは窒素原子を通して互いに付着されて、環構造を形成することができ、Ｒ^４は、２～３個の炭素原子を含有するアルキレンまたはヒドロキシアルキレン基であり、ｎは、０～約２０の範囲である。 Amine oxides are tertiary amine oxides corresponding to the general formula

wherein the arrow is the conventional designation of a semipolar bond, and R ¹ , R ² , and R ³ can be aliphatic, aromatic, heterocyclic, cycloaliphatic, or combinations thereof. Generally, for the amine oxides of the detergents of interest, R ¹ is an alkyl radical of about 8 to about 24 carbon atoms, R ² and R ³ are alkyl or hydroxyalkyls of 1 to 3 carbon atoms, or a mixture thereof, wherein R ² and R ³ can be attached to each other, for example, through an oxygen or nitrogen atom to form a ring structure, and R ⁴ is an alkylene containing 2 to 3 carbon atoms. or a hydroxyalkylene group, where n ranges from 0 to about 20.

Useful water-soluble amine oxide surfactants are selected from coconut or tallow alkyl di-(lower alkyl)amine oxides, specific examples of which are dodecyldimethylamine oxide, tridecyldimethylamine oxide, tetradecyldimethylamine oxide, Pentadecyldimethylamine oxide, hexadecyldimethylamine oxide, heptadecyldimethylamine oxide, octadecyldimethylamine oxide, dodecyldipropylamine oxide, tetradecyldipropylamine oxide, hexadecyldipropylamine oxide, tetradecyldibutylamine oxide, octadecyl dibutylamine oxide, bis(2-hydroxyethyl)dodecylamine oxide, bis(2-hydroxyethyl)-3-dodecoxy-1-hydroxypropylamine oxide, dimethyl-(2-hydroxydodecyl)amine oxide, 3,6,9 -trioctadecyldimethylamine oxide, and 3-dodecoxy-2-hydroxypropyldi-(2-hydroxyethyl)amine oxide.

式中、矢印は、半極性結合の従来の表示であり、Ｒ^１は、１０～約２４個の炭素原子の鎖長範囲のアルキル、アルケニル、またはヒドロキシアルキル部分であり、Ｒ^２およびＲ^３は、それぞれ、１～３個の炭素原子を含有するアルキルまたはヒドロキシアルキル基から別々に選択されるアルキル部分である。 Useful semipolar nonionic surfactants also include water-soluble phosphine oxides having the structure

where the arrow is the conventional designation of a semipolar bond, R ¹ is an alkyl, alkenyl, or hydroxyalkyl moiety ranging in chain length from 10 to about 24 carbon atoms, and R ² and R ³ are , are alkyl moieties independently selected from alkyl or hydroxyalkyl groups containing from 1 to 3 carbon atoms, respectively.

Examples of useful phosphine oxides include dimethyldecylphosphine oxide, dimethyltetradecylphosphine oxide, methylethyltetradecylphosphine oxide, dimethylhexadecylphosphine oxide, diethyl-2-hydroxyoctyldecylphosphine oxide, bis(2-hydroxyethyl) Dodecylphosphine oxide, and bis(hydroxymethyl)tetradecylphosphine oxide.

式中、矢印は、半極性結合の従来の表示であり、Ｒ^１は、約８～約２８個の炭素原子、０～約５個のエーテル結合、および０～約２個のヒドロキシル置換基のアルキルまたはヒドロキシアルキル部分であり、Ｒ^２は、１～３個の炭素原子を有するアルキルおよびヒドロキシアルキル基からなるアルキル部分である。 Semipolar nonionic surfactants useful herein also include water-soluble sulfoxide compounds having the structure

where the arrow is the conventional designation of a semipolar bond and R ¹ is a group of about 8 to about 28 carbon atoms, 0 to about 5 ether linkages, and 0 to about 2 hydroxyl substituents. An alkyl or hydroxyalkyl moiety, where R ² is an alkyl moiety consisting of alkyl and hydroxyalkyl groups having 1 to 3 carbon atoms.

Useful examples of these sulfoxides include dodecylmethylsulfoxide; 3-hydroxytridecylmethylsulfoxide; 3-methoxytridecylmethylsulfoxide; and 3-hydroxy-4-dodecoxybutylmethylsulfoxide.

Semi-polar nonionic surfactants for compositions of the present invention include dimethylamine oxides such as lauryldimethylamine oxide, myristyldimethylamine oxide, cetyldimethylamine oxide, combinations thereof, and the like. Useful water-soluble amine oxide surfactants are selected from octyl, decyl, dodecyl, isododecyl, coconut, or tallow alkyl di-(lower alkyl)amine oxides, specific examples of which are octyldimethylamine oxide, nonyldimethylamine oxide, decyldimethylamine oxide, undecyldimethylamine oxide, dodecyldimethylamine oxide, iso-dodecyldimethylamine oxide, tridecyldimethylamine oxide, tetradecyldimethylamine oxide, pentadecyldimethylamine oxide, hexadecyldimethylamine oxide, hepta Decyldimethylamine oxide, octadecyldimethylamine oxide, dodecyldipropylamine oxide, tetradecyldipropylamine oxide, hexadecyldipropylamine oxide, tetradecyldibutylamine oxide, octadecyldibutylamine oxide, bis(2-hydroxyethyl)dodecylamine oxide, bis(2-hydroxyethyl)-3-dodecoxy-1-hydroxypropylamine oxide, dimethyl-(2-hydroxydodecyl)amine oxide, 3,6,9-trioctadecyldimethylamine oxide, and 3-dodecoxy-2 -hydroxypropyldi-(2-hydroxyethyl)amine oxide.

In some embodiments, the compositions or detergent compositions disclosed herein are free of semi-polar nonionic surfactants.

Cationic Surfactants Surface-active substances are classified as cationic if the charge on the hydrotrope portion of the molecule is positive. Also included in this group are surfactants whose hydrotropes are uncharged unless the pH is lowered to near or below neutrality, but which are then cationic (eg, alkylamines). Theoretically, cationic surfactants can be synthesized from any combination of elements, including the "onium" structure RnX+Y--, compounds other than nitrogen (ammonium) such as phosphorus (phosphonium) and sulfur (sulfonium). can include In fact, the field of cationic surfactants probably has a simple and facile synthetic route to nitrogen cationic surfactants, yielding high yields of products, which is the reason why nitrogen cationic surfactants To make the agent cheaper, it is dominated by nitrogen-containing compounds.

Cationic surfactants preferably comprise, and more preferably refer to, compounds containing at least one long carbon chain hydrophobic group and at least one positively charged nitrogen. The long carbon chain group may be directly attached to the nitrogen atom by simple substitution or, more preferably, indirectly by bridging functional group(s) in so-called interrupted alkylamines and amidoamines. Such functional groups can make the molecule more hydrophilic and/or more water-dispersible, more readily dissolved in water by the co-surfactant mixture, and/or water-soluble. Additional primary, secondary, or tertiary amino groups can be introduced, or the amino nitrogen can be quaternized with a low molecular weight alkyl group for increased water solubility. Additionally, the nitrogen can be part of a branched or linear moiety of varying degrees of unsaturation, or part of a saturated or unsaturated heterocyclic ring. In addition, cationic surfactants may contain complex linkages with two or more cationic nitrogen atoms.

Surfactant compounds, classified as amine oxides, amphoterics and zwitterions, are themselves generally cationic in near-neutral to acidic pH solutions and overlap with the surfactant class. Polyoxyethylated cationic surfactants generally behave like nonionic surfactants in alkaline solutions and like cationic surfactants in acidic solutions.

式中、Ｒは、アルキル鎖を表し、Ｒ’、Ｒ’‘、およびＲ’‘‘は、アルキル鎖もしくはアリール基のいずれか、または水素でもよく、Ｘは、アニオンを表す。アミン塩および第四級アンモニウム化合物は、それらの高い水溶性度のため、本発明における実践的な使用に好ましい。 The simplest cationic amines, amine salts and quaternary ammonium compounds are:

wherein R represents an alkyl chain, R′, R″ and R′″ can be either alkyl chains or aryl groups, or hydrogen, and X represents an anion. Amine salts and quaternary ammonium compounds are preferred for practical use in the present invention due to their high water solubility.

Most bulk commercial cationic surfactants are known to those skilled in the art and are described in "Surfactant Encyclopedia", Cosmetics & Toiletries, Vol. 104(2) 86-96 (1989), can be subdivided into four main classes and additional subgroups. The first class includes alkylamines and their salts. A second class includes the alkyl imidazolines. A third class includes ethoxylated amines. A fourth class includes quaternaries such as, for example, alkylbenzyldimethylammonium salts, alkylbenzene salts, heterocyclic ammonium salts, tetraalkylammonium salts, and the like. Cationic surfactants are known to have a variety of properties that can be beneficial in the present compositions. These desirable properties may include detergency in compositions at or below neutral pH, antimicrobial efficacy, thickening or gelling in conjunction with other agents, and the like.

またはこれらの構造の異性体もしくは混合物によって任意に中断された直鎖または分岐鎖アルキルまたはアルケニル基を含有する有機基であり、これは、約８～２２個の炭素原子を含有する。Ｒ^１基は、追加的に最大１２個のエトキシ基を含有し得る。ｍは、１～３の数字である。好ましくは、分子中の１個以下のＲ^１基は、ｍが２であるときに１６個以上の炭素原子を有するか、またはｍが３であるときに１２個超の炭素原子を有する。各Ｒ^２は、１～４個の炭素原子またはベンジル基を含有するアルキルまたはヒドロキシアルキル基であり、かつ分子中の１個以下のＲ^２は、ベンジルであり、ｘは、０～１１、好ましくは０～６の数である。Ｙ基上の任意の炭素原子位置の残りは、水素によって占められる。 Cationic surfactants useful in the detergent compositions disclosed herein include those having the formula R ¹ _m R ² _{x YL} Z, where each R ¹ has up to 3 optionally substituted with phenyl or hydroxy groups of and up to four of the following structures:

or organic groups containing straight or branched chain alkyl or alkenyl groups optionally interrupted by isomers or mixtures of these structures, which contain about 8 to 22 carbon atoms. The R ¹ group may additionally contain up to 12 ethoxy groups. m is a number from 1 to 3; Preferably, no more than one R ¹ group in the molecule has 16 or more carbon atoms when m is 2, or more than 12 carbon atoms when m is 3. each R ² is an alkyl or hydroxyalkyl group containing 1 to 4 carbon atoms or a benzyl group and no more than 1 R ² in the molecule is benzyl and x is 0 to 11, preferably is a number from 0 to 6. The remainder of any carbon atom positions on the Y group are occupied by hydrogen.

またはこれらの混合物であり得る。好ましくは、Ｌは、１または２であり、かつＹ基は、Ｌが２であるとき、１～約２２個の炭素原子と２個の遊離炭素単結合とを有するＲ^１およびＲ^２類似体（好ましくはアルキレンまたはアルケニレン）から選択される部分によって分離されている。Ｚは、ハロゲン化物アニオン、硫酸アニオン、メチル硫酸アニオン、水酸化物アニオン、または硝酸アニオンなどの水溶性アニオンであり、特に塩化物アニオン、臭化物アニオン、ヨウ化物アニオン、硫酸アニオン、またはメチル硫酸アニオンが多くの中で、カチオン性構成成分の電気的中性を付与するために好ましい。 Y is, but is not limited to,

or mixtures thereof. Preferably, L is 1 or 2 and the Y group, when L is 2, is an R ¹ and R ² analog having 1 to about 22 carbon atoms and 2 free carbon single bonds. (preferably alkylene or alkenylene). Z is a water-soluble anion such as halide, sulfate, methylsulfate, hydroxide or nitrate, especially chloride, bromide, iodide, sulfate or methylsulfate. Among many, it is preferred for imparting electroneutrality of the cationic component.

In some embodiments, the compositions or detergent compositions disclosed herein are free of cationic surfactants.

Amphoteric Surfactants Amphoteric or ampholytic surfactants contain both basic and acidic hydrophilic groups and organic hydrophobic groups. These ionic entities can be either anionic or cationic groups as described herein for other types of surfactants. Basic nitrogen and acidic carboxylate groups are typical functional groups used as basic and acidic hydrophilic groups. In some surfactants, sulfonates, sulfates, phosphonates, or phosphates provide the negative charge.

Amphoteric surfactants are those in which the aliphatic radical can be straight or branched and one of the aliphatic substituents contains about 8 to 18 carbon atoms and one is an anion. They can be broadly described as derivatives of aliphatic secondary and tertiary amines containing water-soluble groups such as carboxy, sulfo, sulfato, phosphato, or phosphono. Amphoteric surfactants are subdivided into two main classes known to those skilled in the art and are described in "Surfactant Encyclopedia" Cosmetics & Toiletries, Vol. 104(2) 69-71 (1989), which is incorporated herein by reference in its entirety. The first class includes acyl/dialkylethylenediamine derivatives (eg, 2-alkylhydroxyethylimidazoline derivatives) and their salts. A second class includes N-alkylamino acids and their salts. Some amphoteric surfactants can be assumed to fit into both classes.

Amphoteric surfactants can be synthesized by methods known to those skilled in the art. For example, 2-alkylhydroxyethylimidazolines are synthesized by condensation and ring closure of long-chain carboxylic acids (or derivatives) with dialkylethylenediamines. Commercial amphoteric surfactants are derivatized by subsequent hydrolysis and ring-opening of the imidazoline ring, eg by alkylation with chloroacetic acid or ethyl acetate. During alkylation, one or two carboxy-alkyl groups react to form tertiary amines and ether linkages, different alkylating agents yielding different tertiary amines.

式中、Ｒは、約８～約１８個の炭素原子を含有する非環式疎水基であり、Ｍは、アニオンの電荷を中和するためのカチオン、一般的にはナトリウムである。本組成物に使用することができる商業的に有名なイミダゾリン由来の両性物質としては、例えば、ココアンホプロピオネート、ココアンホカルボキシ－プロピオネート、ココアンホグリシネート、ココアンホカルボキシ－グリシネート、ココアンホプロピル－スルホネート、およびココアンホカルボキシ－プロピオン酸が挙げられる。アンホカルボン酸は、アンホジカルボン酸のジカルボン酸官能基がジ酢酸および／またはジプロピオン酸である脂肪イミダゾリンから生成することができる。 Long-chain imidazole derivatives having utility in the present invention generally have the following general formula:

wherein R is an acyclic hydrophobic group containing from about 8 to about 18 carbon atoms and M is a cation, typically sodium, to neutralize the charge of the anion. Commercially known imidazoline-derived amphoterics that can be used in the present compositions include, for example, cocoamphopropionate, cocoamphocarboxy-propionate, cocoamphoglycinate, cocoamphocarboxy-glycinate, cocoamphopropyl -sulfonate, and cocoamphocarboxy-propionic acid. Amphodicarboxylic acids can be generated from fatty imidazolines in which the dicarboxylic acid functional group of the amphodicarboxylic acid is diacetic acid and/or dipropionic acid.

The carboxymethylated compounds (glycinates) mentioned herein above are often referred to as betaines. Betaines are a special class of amphoteric substances, discussed herein below in the section entitled Zwitterionic Surfactants.

Long-chain N-alkylamino acids are readily prepared by reaction _RNH2 , where R=C8 _{- C18} straight or branched chain alkyl, aliphatic amines with halogenated carboxylic acids. Alkylation of primary amino groups of amino acids leads to secondary and tertiary amines. Alkyl substituents may have additional amino groups that provide more than one reactive nitrogen center. Most commercial N-alkylamine acids are alkyl derivatives of beta-alanine or beta-N(2-carboxyethyl)alanine. Examples of commercial N-alkylamino acid ampholytes having utility in the present invention include alkyl beta-aminodipropionates, RN(C ₂ H ₄ COOM) ₂ and RNHC ₂ H ₄ COOM. In one embodiment, R can be an acyclic hydrophobic group containing from about 8 to about 18 carbon atoms and M is a cation to neutralize the charge of the anion.

Suitable amphoteric surfactants include those derived from coconut products such as coconut oil or coconut fatty acids. Additional suitable coconut-derived surfactants include ethylenediamine moieties, alkanolamide moieties, amino acid moieties such as glycine, or combinations thereof, and about 8 to 18 (eg, 12 ) of aliphatic substituents on carbon atoms. Such surfactants may also be considered alkyl amphodicarboxylic acids. These amphoteric surfactants are C ₁₂ -alkyl-C(O)-NH-CH ₂ -CH ₂ -N ⁺ (CH ₂ -CH ₂ -CO ₂ Na) ₂ -CH ₂ -CH ₂ -OH or C ₁₂ -alkyl-C(O)-N(H)-CH ₂ -CH ₂ -N ⁺ (CH ₂ -CO ₂ Na) ₂ -CH ₂ -CH ₂ -OH . Disodium cocoamphodipropionate is one suitable amphoteric surfactant and is available from Rhodia Inc. , Cranbury, N.; J. under the trade name Miranol(TM) FBS. Another suitable coconut-derived amphoteric surfactant having the chemical name disodium cocoamphodiacetate is also available from Rhodia Inc.; , Cranbury, N.; J. under the tradename Mirataine™ JCHA.

A representative list of the amphoteric class and species of these surfactants is described in US Pat. No. 3,929,678, issued Dec. 30, 1975 to Laughlin and Heuring. Further examples are described in "Surface Active Agents and Detergents" (Vol. I and II by Schwartz, Perry and Berch). Each of these references is hereby incorporated by reference in its entirety.

In some embodiments, the compositions or detergent compositions disclosed herein are free of amphoteric surfactants.

Zwitterionic Surfactants Zwitterionic surfactants can be viewed as a subset of amphoteric surfactants and can contain an anionic charge. Zwitterionic surfactants are derivatives of secondary and tertiary amines, derivatives of heterocyclic secondary and tertiary amines, or quaternary ammonium, quaternary phosphonium, or tertiary sulfonium It can be broadly described as a derivative of the compound. Typically, zwitterionic surfactants contain a positively charged quaternary ammonium, or in some cases a sulfonium or phosphonium ion, a negatively charged carboxyl group, and an alkyl group. Zwitterionic surfactants generally contain cationic and anionic groups that ionize to approximately equal extent in the isoelectric region of the molecule and can generate strong "inner salt" attraction between positive and negative charge centers. . Examples of such zwitterionic synthetic surfactants include derivatives of aliphatic quaternary ammonium, phosphonium, and sulfonium compounds, where the aliphatic radical can be linear or branched, aliphatic substituted One of the groups contains 8-18 carbon atoms and one contains an anionic water solubilizing group such as carboxy, sulfonate, sulfate, phosphate, or phosphonate.

であり、式中、Ｒ^１は、０～１０個のエチレンオキシド部分および０～１個のグリセリル部分を有する８～１８個の炭素原子のアルキル、アルケニル、またはヒドロキシアルキルラジカルを含有し、Ｙは、窒素、リン、および硫黄原子からなる群から選択され、Ｒ^２は、１～３個の炭素原子を含有するアルキルまたはモノヒドロキシアルキル基であり、ｘは、Ｙが硫黄原子であるとき１であり、Ｙが窒素またはリン原子であるとき２であり、Ｒ^３は、１～４個の炭素原子のアルキレンまたはヒドロキシアルキレンまたはヒドロキシアルキレンであり、Ｚは、カルボキシレート、スルホネート、サルフェート、ホスホネート、およびホスフェート基からなる群から選択されるラジカルである。 Betaine and sultaine surfactants are exemplary zwitterionic surfactants for use herein. The general formula for these compounds is

wherein R ¹ contains an alkyl, alkenyl, or hydroxyalkyl radical of 8-18 carbon atoms having 0-10 ethylene oxide moieties and 0-1 glyceryl moieties, and Y is selected from the group consisting of nitrogen, phosphorus, and sulfur atoms, R ² is an alkyl or monohydroxyalkyl group containing 1 to 3 carbon atoms, and x is 1 when Y is a sulfur atom; , 2 when Y is a nitrogen or phosphorus atom, R ³ is alkylene or hydroxyalkylene or hydroxyalkylene of 1 to 4 carbon atoms, Z is carboxylate, sulfonate, sulfate, phosphonate, and phosphate is a radical selected from the group consisting of groups.

Examples of zwitterionic surfactants having the above structures include 4-[N,N-di(2-hydroxyethyl)-N-octadecylammonio]-butane-1-carboxylate, 5-[S- 3-hydroxypropyl-S-hexadecylsulfonio]-3-hydroxypentane-1-sulfate, 3-[P,P-diethyl-P-3,6,9-trioxatetracosanephosphonio]-2-hydroxy Propane-1-phosphate, 3-[N,N-dipropyl-N-3-dodecoxy-2-hydroxypropyl-ammonio]-propane-1-phosphonate, 3-(N,N-dimethyl-N-hexadecylammonio )-propane-1-sulfonate, 3-(N,N-dimethyl-N-hexadecylammonio)-2-hydroxy-propane-1-sulfonate, 4-[N,N-di(2(2-hydroxyethyl )-N(2-hydroxydodecyl)ammonio]-butane-1-carboxylate, 3-[S-ethyl-S-(3-dodecoxy-2-hydroxypropyl)sulfonio]-propane-1-phosphate, 3-[ P,P-dimethyl-P-dodecylphosphonio]-propane-1-phosphonate and S[N,N-di(3-hydroxypropyl)-N-hexadecylammonio]-2-hydroxy-pentane-1- Alkyl groups contained in the detergent surfactants may be linear or branched and saturated or unsaturated.

Zwitterionic surfactants suitable for use in the present compositions include betaines of the general structure:

These surfactant betaines typically do not exhibit strong cationic or anionic character at extreme pH or show reduced water solubility in their isoelectric range. Unlike "external" quaternary ammonium salts, betaines are capable of symbiosis with anions. Examples of suitable betaines include coconut acylamidopropyldimethylbetaine, hexadecyldimethylbetaine, C _12-14 acylamidopropyl betaine, C _8-14 acylamidohexyldiethylbetaine, 4-C _14-16 acylmethylamide diethylammonium o-1-carboxybutane, C _16-18 acylamidodimethylbetaine, C _12-16 acylamidopentanediethylbetaine, and C _12-16 acylmethylamidodimethylbetaine.

Sultanes useful in the present invention include compounds having the formula (R(R ¹ ) ₂ N ⁺ R ² SO ^3- , where R is a C ₆ -C ₁₈ hydrocarbyl group and each R ¹ is typically independently C ₁ -C ₃ alkyl, eg methyl, and R ² is a C ₁ -C ₆ hydrocarbyl group, eg a C ₁ -C ₃ alkylene or hydroxyalkylene group.

A representative list of the zwitterionic class and these surfactant species is described in US Pat. No. 3,929,678, issued Dec. 30, 1975 to Laughlin and Heuring. Further examples are described in "Surface Active Agents and Detergents" (Vol. I and II by Schwartz, Perry and Berch). Each of these references is incorporated herein in its entirety.

In some embodiments, the compositions or detergent compositions disclosed herein are free of zwitterionic surfactants.

Gemini Surfactants Conventional surfactants generally have one hydrophilic group and one hydrophobic group, whereas gemini surfactants have at least two hydrophobic groups and at least two hydrophilic groups. These surfactants have the general formula: A1-G-A2 and are so named because they contain two surfactant moieties (A1, A2) joined by a spacer (G), each interface The activator portion (A1, A2) has a hydrophilic group and a hydrophobic group. Generally the two surfactant moieties (A1, A2) are the same, but they may be different.

Gemini surfactants can be anionic, nonionic, cationic, or amphoteric. The hydrophilic and hydrophobic groups of each surfactant moiety (A1, A2) can be any of those known to be used in conventional surfactants having one hydrophilic group and one hydrophobic group. For example, typical nonionic gemini surfactants, such as bis-polyoxyethylene alkyl ethers, contain two polyoxyethylene alkyl ether moieties.
Each portion contains a hydrophilic group, such as polyethylene oxide, and a hydrophobic group, such as an alkyl chain.

式中、Ｒ^３０は独立して、Ｃ_１～Ｃ_２２アルキル、Ｒ^３４－－Ｃ（Ｏ）－－またはＲ^３４－－Ｂ－Ｒ^３５－－であり、Ｒ^３４は、Ｃ_１～Ｃ_２２アルキルであり、Ｒ^３５は、Ｃ_１～Ｃ_１２アルキルであり、Ｂは、アミド基、－－Ｃ（Ｏ）Ｎ（Ｒ^３６）－－、アミノ基－－Ｎ（Ｒ^３６）－－、カルボキシル基－－Ｃ（Ｏ）－－Ｏ－－、カルボニル基、またはポリエーテル基－－（ＥＯ）_ａ（ＰＯ）_ｂ－－であり、ＥＯは、エチレンオキシラジカルを表し、ＰＯは、プロピレンオキシラジカルを表し、ａおよびｂは、０～１００の数であり、ａは、好ましくは約０～約３０であり、ｂは、好ましくは約０～１０であり、ａプラスｂは、少なくとも１であり、ＥＯおよびＰＯラジカルは、ランダムに混合され得るか、または個別のブロック内にあってもよく、Ｒ^３６は、水素またはＣ_１～Ｃ_６アルキルである。 Anionic and nonionic gemini surfactants include those of the formula:

wherein R ³⁰ is independently C ₁ -C ₂₂ alkyl, R ³⁴ --C(O)-- or R ³⁴ --B--R ³⁵ --, and R ³⁴ is C ₁ -C ₂₂ alkyl, R ³⁵ is C ₁ -C ₁₂ alkyl, B is amido group, --C(O)N(R ³⁶ )--, amino group --N(R ³⁶ )--, carboxyl a group --C(O)--O--, a carbonyl group, or a polyether group --(EO) _a (PO) _b --, EO representing an ethyleneoxy radical and PO a propyleneoxy radical wherein a and b are numbers from 0 to 100, a is preferably from about 0 to about 30, b is preferably from about 0 to 10, a plus b is at least 1 , EO and PO radicals may be randomly mixed or in separate blocks, and R ³⁶ is hydrogen or C ₁ -C ₆ alkyl.

R ³¹ is independently hydrogen or C ¹ -C ₂₂ alkyl and R ³² is independently C ₁ -C ₁₀ alkyl, --O--, amido group --C(O)N(R ₆ )—, a polyether group —O(EO) _a (PO) _b —, —R ³⁷ —D—R ³⁷ —, or —D—R ³⁷ —D—, wherein R ³⁷ is independently C ₁ -C ₆ alkyl, D is -O-, -S-, an amide group -C(O)N(R ³⁶ )-, or an amino group -N(R ³⁶ )-, and R ³⁶ , a, and b are as defined above, and t is independently 0 or 1.

Z is independently hydrogen, --SO ₃ Y, --P(O)(OY) ₂ , --COOY, --CH ₂ COOY, --CH ₂ CH(OH)CH ₂ SO ₃ Y; , when R ³² is not a polyether, Z is also --OSO ₃ Y and --OP(O)(OY) ₂ and Y is hydrogen, an alkali metal such as sodium and potassium; ammonium; or organic base salts such as monoethanolamine, diethanolamine, triethanolamine, triethylamine, trimethylamine, N-hydroxyethylmorpholine.

A1 or A2 is independently a linear or branched C ₁ -C ₆ alkyl, O--R ₅ --O-- group or aryl, preferably phenyl, and R ³³ is a bond, phenyl or diphenyl aryl groups such as groups, C ₁ -C ₁₀ alkyl groups, preferably C ₁ -C ₄ alkyl groups, most preferably methylene, —C≡C—, —O—, —S—, —S— S--, --N(R ³⁶ )--, --R ³⁵ O--, --R ³⁵ O(EO) _a (PO) _b --, --D ₁ --R ³⁸ --D ₁ -- —, or —R ³⁸ —D ₁ —R ³⁸ —, where R ³⁸ is independently a C ₁ -C ₁₀ alkyl group, —C(O)—, —R ³⁵ O(EO) _a (PO) _b --, --OR ³⁵ --O--, or aryl, such as phenyl, and D ₁ is independently --O--, --S--, -- S--S--, --SO ₂ --, --C(O)--, polyether group --O(EO) _a (PO) _b --, amide group --C(O)N( R ³⁶ )--, an amino group --N(R ³⁶ )--, --O--R ₅ --O--, or aryl, wherein R ³⁵ , R ³⁶ , a, and b are defined above It is as it was.

In the formulas of this disclosure, the term "alkali" includes substituted alkalis, particularly hydroxy-substituted derivatives thereof, as well as straight and branched chains. When Z is hydrogen, the gemini surfactants are nonionic.

式中、Ｒ_ｃは、アリール、好ましくは、フェニルを表す。Ｒ^３１、Ｒ^３３、Ｒ^３４、およびＺは、上記で定義されたとおりである。ａおよびｂは、０～１００の数であり、ａは、好ましくは約０～約３０であり、ｂは、好ましくは約０～１０であり、ａプラスｂは、少なくとも１であり、ＥＯおよびＰＯラジカルは、ランダムに混合され得るか、または別個のブロック内にあってもよい。 Other gemini surfactants that are particularly useful in this disclosure include gemini anionic or nonionic surfactants of the formula:

In the formula, R _c represents aryl, preferably phenyl. R ³¹ , R ³³ , R ³⁴ and Z are as defined above. a and b are numbers from 0 to 100, a is preferably from about 0 to about 30, b is preferably from about 0 to 10, a plus b is at least 1, EO and The PO radicals can be randomly mixed or can be in separate blocks.

The primary hydroxyl groups of these surfactants can be readily phosphorylated, sulfated, or carboxylated by standard techniques.

In some embodiments, the compositions or detergent compositions disclosed herein do not contain gemini surfactants.

Additional Corrosion Inhibitors In some embodiments, the corrosion control compositions disclosed herein further comprise additional corrosion inhibitors. In some other embodiments, the corrosion control compositions disclosed herein further comprise additional corrosion inhibitors and carriers. In some other embodiments, the corrosion control compositions disclosed herein further comprise additional corrosion inhibitors, biocides, and carriers. In some embodiments, the control compositions disclosed herein comprise one or more dicationic or dianionic compounds disclosed herein, one or more additional corrosion inhibitors, and a carrier. can be. In some embodiments, the corrosion control compositions disclosed herein comprise one or more of the dicationic or dianionic compounds disclosed herein, a carrier, an additional corrosion inhibitor, and a biocide. consists of

The corrosion control composition is one of from about 0.1% to about 20%, from about 0.1% to about 10%, or from 0.1% to about 5% by weight based on the total weight of the composition. Additional corrosion inhibitors as described above may be included. The compositions of the present invention may contain from 0 to 10 weight percent, based on the total weight of the composition, of one or more additional corrosion inhibitors. The composition contains about 1.0 wt%, about 1.5 wt%, about 2.0 wt%, about 2.5 wt%, about 3.0 wt%, about 3.0 wt%, based on the total weight of the composition. 5 wt%, about 4.0 wt%, about 4.5 wt%, about 5.0 wt%, about 5.5 wt%, about 6.0 wt%, about 6.5 wt%, about 7.0 wt% % by weight, about 7.5% by weight, about 8.0% by weight, about 8.5% by weight, about 9.0% by weight, about 9.5% by weight, about 10.0% by weight, about 10.5% by weight %, about 11.0 wt%, about 11.5 wt%, about 12.0 wt%, about 12.5 wt%, about 13.0 wt%, about 13.5 wt%, about 14.0 wt% , about 14.5% by weight, or about 15.0% by weight, or any value or range therebetween. A particular water system may have its own requirements for using one or more additional corrosion inhibitors, and the weight percent of one or more additional corrosion inhibitors in the composition may vary may vary depending on the water system used.

Corrosion inhibitors for polymetallic protection are typically, but not limited to, triazoles such as benzotriazoles, halogenated triazoles, and nitro-substituted azoles.

The one or more additional corrosion inhibitors can be imidazoline compounds, quaternary ammonium compounds, pyridinium compounds, or combinations thereof.

The one or more additional corrosion inhibitors can be imidazolines. Imidazolines can be, for example, imidazolines derived from diamines such as ethylenediamine (EDA), diethylenetriamine (DETA), triethylenetetramine (TETA) and long chain fatty acids such as tall oil fatty acid (TOFA). The imidazoline can be an imidazoline or imidazoline derivative of formula (1A). Representative imidazoline derivatives include imidazolinium compounds of formula (2A) or bisquaternized compounds of formula (3A).

式中、Ｒ^１０ａは、Ｃ_１～Ｃ_２０アルキル基またはＣ_１～Ｃ_２０アルコキシアルキル基であり、Ｒ^１１ａは、水素、Ｃ_１～Ｃ_６アルキル、Ｃ_１～Ｃ_６ヒドロキシアルキル、またはＣ_１～Ｃ_６アリールアルキルであり、Ｒ^１２ａおよびＲ^１３ａは、独立して、水素またはＣ_１～Ｃ_６アルキル基である。好ましくは、イミダゾリンは、トール油脂肪酸（ＴＯＦＡ）に典型的なアルキル混合物であるＲ^１０ａを含み、Ｒ^１１ａ、Ｒ^１２ａ、およびＲ^１３ａは、各々水素である。 The one or more additional corrosion inhibitors may include imidazolines of formula (1A),

wherein R ^10a is a C ₁ -C ₂₀ alkyl group or a C ₁ -C ₂₀ alkoxyalkyl group, R ^11a is hydrogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ hydroxyalkyl, or C ₁ -C ₆ arylalkyl, and R ^12a and R ^13a are independently hydrogen or C ₁ -C ₆ alkyl groups. Preferably, the imidazoline contains R ^10a , an alkyl mixture typical of tall oil fatty acids (TOFA), and R ^11a , R ^12a and R ^13a are each hydrogen.

式中、Ｒ^１０ａは、Ｃ_１～Ｃ_２０アルキル基またはＣ_１～Ｃ_２０アルコキシアルキル基であり、Ｒ^１１ａおよびＲ^１４ａは、独立して、水素、Ｃ_１～Ｃ_６アルキル、Ｃ_１～Ｃ_６ヒドロキシアルキル、またはＣ_１～Ｃ_６アリールアルキルであり、Ｒ^１２ａおよびＲ^１３ａは、独立して、水素またはＣ_１～Ｃ_６アルキル基であり、Ｘ^－は、ハロゲン化物（塩化物、臭化物、ヨウ化物など）、炭酸塩、スルホン酸塩、リン酸塩、または有機カルボン酸（酢酸塩など）のアニオンである。好ましくは、イミダゾリニウム化合物は、１－ベンジル－１－（２－ヒドロキシエチル）－２－トール油－２－イミダゾリニウムクロリドを含む。 The one or more additional corrosion inhibitors can be imidazolinium compounds of formula (2A),

wherein R ^10a is a C ₁ -C ₂₀ alkyl group or a C ₁ -C ₂₀ alkoxyalkyl group, R ^11a and R ^14a are independently hydrogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ hydroxyalkyl, or C ₁ -C ₆ arylalkyl, R ^12a and R ^13a are independently hydrogen or C ₁ -C ₆ alkyl groups, X ^- is halide (chloride, bromide, iodide, etc.), carbonate, sulfonate, phosphate, or the anion of an organic carboxylic acid (such as acetate). Preferably, the imidazolinium compound comprises 1-benzyl-1-(2-hydroxyethyl)-2-toll oil-2-imidazolinium chloride.

式中、Ｒ_１ａおよびＲ_２ａはそれぞれ独立して、１～約２９個の炭素原子を有する、非置換の分岐鎖、鎖状、もしくは環式アルキルもしくはアルケニル；１～約２９個の炭素原子を有する、部分的もしくは完全に酸素化、硫化、および／もしくはリン酸化された分岐鎖、鎖状、もしくは環式アルキルもしくはアルケニル；またはそれらの組み合わせであり、Ｒ_３ａおよびＲ_４ａはそれぞれ独立して、１～約２９個の炭素原子を有する、非置換の分岐鎖、鎖状、もしくは環式アルキレンもしくはアルケニレン；１～約２９個の炭素原子を有する、部分的もしくは完全に酸素化、硫化、および／もしくはリン酸化された分岐鎖、鎖状、もしくは環式アルキレンもしくはアルケニレン；またはそれらの組み合わせであり、Ｌ_１およびＬ_２はそれぞれ独立して、存在しないか、Ｈ、－ＣＯＯＨ、－ＳＯ_３Ｈ、－ＰＯ_３Ｈ、－ＣＯＯＲ^５ａ、－ＣＯＮＨ_２、－ＣＯＮＨＲ^５ａ、または－－ＣＯＮ（Ｒ^５ａ）_２であり、Ｒ_５ａはそれぞれ独立して、１～約１０個の炭素原子を有する分岐鎖または非分岐鎖アルキル、アリール、アルキルアリール、アルキルヘテロアリール、シクロアルキル、またはヘテロアリール基であり、ｎは、０または１であり、ｎが０のとき、Ｌ_２は、存在しないか、またはＨであり、ｘは、１～約１０であり、ｙは、１～約５である。好ましくは、Ｒ^１ａおよびＲ^２ａは、それぞれ独立して、Ｃ６～Ｃ２２アルキル、Ｃ_８～Ｃ_２０アルキル、Ｃ_１２～Ｃ_１８アルキル、Ｃ_１６～Ｃ_１８アルキル、もしくはそれらの組み合わせであり、Ｒ^３ａおよびＲ^４ａは、Ｃ_１～Ｃ_１０アルキレン、Ｃ_２～Ｃ_８アルキレン、Ｃ_２～Ｃ_６アルキレン、またはＣ_２～Ｃ_３アルキレンであり、ｎは０もしくは１であり、ｘは２であり、ｙは１であり、Ｒ_３およびＲ_４は－Ｃ_２Ｈ_２－であり、Ｌ_１は－ＣＯＯＨ、－ＳＯ_３Ｈ、もしくは－ＰＯ_３Ｈであり、Ｌ_２は存在しないか、Ｈ、－ＣＯＯＨ、－ＳＯ_３Ｈ、もしくは－ＰＯ_３Ｈである。例えば、Ｒ^１ａおよびＲ^２ａは、トール油脂肪酸の混合物から誘導することができ、主としてＣ１７Ｈ３３およびＣ_１７Ｈ_３１の混合物であるか、またはＣ_１６～Ｃ_１８アルキルであり得；Ｒ^３ａおよびＲ^４ａは、Ｃ_２～Ｃ_３アルキレン、例えば－Ｃ_２Ｈ_２－であり得；ｎは、１であり、かつＬ_２は、－ＣＯＯＨであるか、またはｎは、０であり、かつＬ_２は、存在しないかもしくはＨであり；ｘは２であり；ｙは１であり；Ｒ^３ａおよびＲ^４ａは、－Ｃ_２Ｈ_２であり；Ｌ_１は、－ＣＯＯＨである。 The one or more additional corrosion inhibitors can be a bisquaternized compound having the formula (3A),

wherein R _1a and R _2a are each independently an unsubstituted branched, chain, or cyclic alkyl or alkenyl having from 1 to about 29 carbon atoms; a partially or fully oxygenated, sulfurized, and/or phosphorylated branched, chain, or cyclic alkyl or alkenyl having; or combinations thereof, wherein R _3a and R _4a each independently unsubstituted branched, chain, or cyclic alkylene or alkenylene having from 1 to about 29 carbon atoms; partially or fully oxygenated, sulfurized, and/or having from 1 to about 29 carbon atoms; or a phosphorylated branched, chain, or cyclic alkylene or alkenylene; or a combination thereof, wherein L ₁ and L ₂ are each independently absent, H, —COOH, —SO ₃ H, —PO ₃ H, —COOR ^5a , —CONH ₂ , —CONHR ^5a , or —CON(R ^5a ) ₂ , wherein each R _5a is independently a branched chain or is an unbranched alkyl, aryl, alkylaryl, alkylheteroaryl, cycloalkyl, or heteroaryl group, n is 0 or 1, and when n is 0, L ₂ is absent or is H and x is from 1 to about 10 and y is from 1 to about 5. Preferably, R ^1a and R ^2a are each independently C6-C22 alkyl, C ₈ -C ₂₀ alkyl, C ₁₂ -C ₁₈ alkyl, C ₁₆ -C ₁₈ alkyl, or a combination thereof, and R ^3a and R ^4a is C ₁ -C ₁₀ alkylene, C ₂ -C ₈ alkylene, C ₂ -C ₆ alkylene, or C ₂ -C ₃ alkylene, n is 0 or 1, x is 2, y is 1, R ₃ and R ₄ are —C ₂ H ₂ —, L ₁ is —COOH, —SO ₃ H, or —PO ₃ H, and L ₂ is absent, H, — COOH, —SO ₃ H, or —PO ₃ H. For example, R ^1a and R ^2a can be derived from a mixture of tall oil fatty acids, can be a mixture of predominantly C17H33 and C ₁₇ H ₃₁ , or can be C ₁₆ -C ₁₈ alkyl; R ^3a and R ^4a may be C ₂ -C ₃ alkylene, such as —C ₂ H ₂ —; n is 1 and L ₂ is —COOH, or n is 0 and L ₂ is , is absent or is H; x is 2; y is ₁ ; R ^3a and R ^4a are -C ₂ H ₂ ;

It is understood that the number of carbon atoms specified for each group of formula (3A) refers to the backbone of carbon atoms and does not include carbon atoms that may be contributed by substituents.

The one or more additional corrosion inhibitors can be a bisquaternized imidazoline compound having the formula (3A), where R ^1a and R ^2a are each independently C ₆ -C ₂₂ alkyl, C ₈ C ₂₀ alkyl, C ₁₂ -C ₁₈ alkyl, or C ₁₆ -C ₁₈ alkyl, or combinations thereof, and R ^4a is C ₁ -C ₁₀ alkylene, C ₂ -C ₈ alkylene, C ₂ -C ₆ alkylene, or C ₂ -C ₃ alkylene, x is 2, y is 1, n is 0, L ₁ is —COOH, —SO ₃ H, or —PO ₃ H and L ₂ is either absent or H. Preferably, the bis-quaternized compound has the formula (3A), wherein R ^1a and R ^2a are each independently C ₁₆ -C ₁₈ alkyl and R ^4a is —C ₂ H ₂ -, x is 2, y is 1, n is 0, L ₁ is -COOH, -SO ₃ H, or -PO ₃ H, L ₂ is present No or H.

式中、Ｒ^１ａ、Ｒ^２ａ、およびＲ^３ａは、独立して、Ｃ_１～Ｃ_２０アルキルであり、Ｒ^４ａは、メチルまたはベンジルであり、Ｘ^－は、ハロゲン化物またはメトサルフェートである。 The one or more additional corrosion inhibitors may include a quaternary ammonium compound of formula (4A),

wherein R ^1a , R ^2a and R ^3a are independently C ₁ -C ₂₀ alkyl, R ^4a is methyl or benzyl, and X ^- is halide or methosulfate.

Suitable alkyl, hydroxyalkyl, alkylaryl, arylalkyl, or arylamine quaternary salts include alkylaryl, arylalkyl, and arylamine quaternary salts of the formula [N ⁺ R ^5a R ^6a R ^7a R ^8a ][X ⁻ ]. class salts, where R ^5a , R ^6a , R ^7a , and R ^8a contain 1-18 carbon atoms and X is Cl, Br, or I; For quaternary salts, R ^5a , R ^6a , R ^7a , and R ^8a are each independently alkyl (eg, C ₁ -C ₁₈ alkyl), hydroxyalkyl (eg, C ₁ -C ₁₈ hydroxyalkyl), and It can be arylalkyl (eg, benzyl). Monocyclic or polycyclic aromatic amine salts with alkyl or alkylaryl halides include salts of the formula [N ⁺ R ^5a R ^6a R ^7a R ^8a ][X ⁻ ], wherein R ^5a , R ^6a 1 , R ^7a , and R ^8a contain 1-18 carbon atoms and at least one aryl group, and X is Cl, Br, or I;

Suitable quaternary ammonium salts include tetramethylammonium, tetraethylammonium, tetrapropylammonium, tetrabutylammonium, tetrahexylammonium, tetraoctylammonium, benzyltrimethylammonium, benzyltriethylammonium, phenyltrimethyl ammonium salts, phenyltriethylammonium salts, cetylbenzyldimethylammonium salts, hexadecyltrimethylammonium salts, dimethylalkylbenzyl quaternary ammonium salts, monomethyldialkylbenzyl quaternary ammonium salts, or trialkylbenzyl quaternary ammonium salts (wherein the above alkyl groups are , having from about 6 to about 24 carbon atoms, from about 10 to about 18 carbon atoms, or from about 12 to about 16 carbon atoms). The quaternary ammonium salt can be a benzyltrialkyl quaternary ammonium salt, a benzyltriethanolamine quaternary ammonium salt, or a benzyldimethylaminoethanolamine quaternary ammonium salt.

式中、Ｒ^９ａは、アルキル基、アリール基、またはアリールアルキル基であり、当該アルキル基は、１～約１８個の炭素原子を有し、Ｘ^－は、塩化物、臭化物、またはヨウ化物などのハロゲン化物である。これらの化合物の中には、アルキルピリジニウム塩およびアルキルピリジニウムベンジル四級物がある。例示的な化合物としては、メチルピリジニウムクロリド、エチルピリジニウムクロリド、プロピルピリジニウムクロリド、ブチルピリジニウムクロリド、オクチルピリジニウムクロリド、デシルピリジニウムクロリド、ラウリルピリジニウムクロリド、セチルピリジニウムクロリド、ベンジルピリジニウムクロリド、およびアルキルベンジルピリジニウムクロリドが挙げられ、好ましくは、アルキルは、Ｃ_１～Ｃ_６ヒドロカルビル基である。好ましくは、ピリジニウム化合物は、ベンジルピリジニウムクロリドを含む。 The one or more additional corrosion inhibitors can be pyridinium, such as those represented by formula (5A),

wherein R ^9a is an alkyl group, an aryl group, or an arylalkyl group, wherein the alkyl group has from 1 to about 18 carbon atoms, and X ^- is chloride, bromide, or iodide, etc. is a halide of Among these compounds are alkylpyridinium salts and alkylpyridinium benzyl quaternaries. Exemplary compounds include methylpyridinium chloride, ethylpyridinium chloride, propylpyridinium chloride, butylpyridinium chloride, octylpyridinium chloride, decylpyridinium chloride, laurylpyridinium chloride, cetylpyridinium chloride, benzylpyridinium chloride, and alkylbenzylpyridinium chloride. and preferably the alkyl is a C ₁ -C ₆ hydrocarbyl group. Preferably, the pyridinium compound comprises benzylpyridinium chloride.

The one or more additional corrosion inhibitors can be phosphate esters, monomeric or oligomeric fatty acids, alkoxylated amines, or mixtures thereof.

The one or more additional corrosion inhibitors can be phosphate esters. Suitable mono-, di-, and tri-alkyl and alkylaryl phosphates and phosphates of mono-, di-, and triethanolamine typically contain from 1 to about 18 carbon atoms. contains. Preferred mono-, di-, and trialkyl phosphates, alkylaryl, or arylalkyl phosphates are those prepared by reacting a C ₃ -C ₁₈ fatty alcohol with phosphorus pentoxide. The phosphate ester intermediate exchanges its ester group with triethyl phosphate to produce a broader distribution of alkyl phosphates.

Alternatively, phosphate esters can be made by blending an alkyl diester with a mixture of low molecular weight alkyl alcohols or diols. Low molecular weight alkyl alcohols or diols preferably include C ₆ -C ₁₀ alcohols or diols. Furthermore, phosphoric esters of polyols containing one or more 2-hydroxyethyl groups and their salts, and hydroxylamines obtained by reacting polyphosphoric acid or phosphorus pentoxide with hydroxylamines such as diethanolamine or triethanolamine Phosphate esters are preferred.

The one or more additional corrosion inhibitors can be monomeric or oligomeric fatty acids. Preferred monomeric or oligomeric fatty acids are C ₁₄ -C ₂₂ saturated and unsaturated fatty acids, and dimer, trimer and oligomer products obtained by polymerizing one or more of such fatty acids.

The one or more additional corrosion inhibitors can be alkoxylated amines. Alkoxylated amines can be ethoxylated alkylamines. The alkoxylated amine can be an ethoxylated tallow amine.

In some embodiments, additional corrosion inhibitors in the corrosion control composition are tall oil diethylenetriamine imidazoline, 1-(2-hydroxyethyl)-2-coconut oil-2-imidazoline, 1-benzyl-1-( 2-hydroxyethyl)-2-coconut oil-2-imidazolinium chloride, benzyl-dimethyl-dodecyl-ammonium chloride, N-cocoalkyl 1,3, propylenediamine acetate, morpholine, morpholine derivatives, didecyl-dimethyl-ammonium chloride , 1-benzyl-1-(2-hydroxyethyl)-2-toll oil-2-imidazolinium chloride, and N-benzyl-alkylpyridinium chloride, tall oil fatty acid, trimer C18 unsaturated fatty acid, dimer C18 unsaturated fatty acids, alkylpyridines, N-benzyl-alkylpyridinium chlorides, quinolines, quinoline quaternaries with benzyl chlorides, or mixtures thereof.

Dispersants In some embodiments, the corrosion control compositions disclosed herein can further comprise a dispersant. Dispersants keep particulate matter present in the water of an aqueous system dispersed and prevent it from agglomerating. The composition can include about 0.1-10%, about 0.5-5%, or about 0.5-4% by weight of dispersant based on the total weight of the composition.

Dispersants can be acrylic acid polymers, maleic acid polymers, copolymers of acrylic acid and sulfonated monomers, alkyl esters thereof, or combinations thereof. These polymers may include terpolymers of acrylic acid, acrylamide, and sulfonated monomers. These polymers can also include quaternary polymers consisting of acrylic acid and three other monomers.

Suitable dispersants include aliphatic phosphonic acids having 2 to 50 carbons, such as hydroxyethyldiphosphonic acid, and aminoalkylphosphonic acids, such as polyaminomethylene phosphonates having 2 to 10 N atoms, such as , each having at least one methylene phosphonic acid group), examples of the latter having 2 to 4 methylene groups between each N atom, methylene ethylenediaminetetra(methylenephosphonate), diethylenetriaminepenta(methylenephosphonate), and triamine- and tetraamine-polymethylenephosphonates, differing in at least two of the number of groups. Other suitable dispersants include lignin or derivatives of lignin such as lignosulfonates, and naphthalenesulfonic acid and derivatives.

In some embodiments, the dispersant in the corrosion control compositions disclosed herein is the reaction product of tall oil fatty acid with diethylenetriamine and acrylic acid (1:1:1), fatty acid or tall oil with Reaction products with triethylenetetramine or tetraethylenepentamine, reaction products of diethylenetriamine and naphthenic acid.

Corrosion control compositions include mercaptoalkyl alcohol, mercaptoacetic acid, thioglycolic acid, 3,3'-dithiodipropionic acid, sodium thiosulfate, thiourea, L-cysteine, tert-butyl mercaptan, sodium thiosulfate, ammonium thiosulfate, It can further include an organic sulfur compound such as sodium thiocyanate, ammonium thiocyanate, sodium metabisulfite, or combinations thereof. Preferably, the mercaptoalkyl alcohol includes 2-mercaptoethanol. Such compounds are used as synergists in compositions.

In some embodiments, the organic sulfur compound in the corrosion control composition is 2-mercaptoethanol, sodium thiosulfate, thioglycolic acid, or mixtures thereof.

The organosulfur compound comprises from about 0.5% to about 15%, preferably from about 1% to about 10%, more preferably from about 1% to about 10%, by weight of the composition, based on the total weight of the composition. 5% by weight. The organosulfur compound comprises about 1%, about 2%, about 3%, about 4%, about 5%, about 6%, about 7%, about 8%, about 9%, by weight of the composition. %, about 10%, about 11%, about 12%, about 13%, about 14%, or about 15%.

The corrosion control composition can further include a demulsifier. Preferably, the demulsifier comprises an oxyalkylate polymer such as polyalkylene glycol. The demulsifier comprises from about 0.1% to about 10%, from about 0.5% to about 5%, or from about 0.5% to about 4%, by weight of the composition, based on the total weight of the composition. weight percent. The demulsifier may comprise about 0.5%, about 1%, about 1.5%, about 2%, about 2.5%, about 3%, about 3.5%, by weight of the composition; It can comprise about 4 wt%, about 4.5 wt%, or about 5 wt%.

The corrosion control composition can further include an asphaltene inhibitor. The composition comprises from about 0.1% to about 10%, from about 0.1% to about 5%, or from about 0.5% to about 4% by weight of asphaltenes, based on the total weight of the composition. An inhibitor may be included. Suitable asphaltene inhibitors include aliphatic sulfonic acids, alkylarylsulfonic acids, arylsulfonates, lignosulfonates, alkylphenol/aldehyde resins and similar sulfonated resins, polyolefin esters, polyolefinimides, alkyl, alkylenephenyl or alkylenepyridyl functional groups. polyolefin amides with alkyl, alkylenephenyl or alkylenepyridyl functionalities, polyolefinimides with alkyl, alkylenephenyl or alkylenepyridyl functionalities, alkenyl/vinylpyrrolidone copolymers, polyolefins with maleic anhydride or vinylimidazole , hyperbranched polyester amides, polyalkoxylated asphaltenes, amphoteric fatty acids, salts of alkyl succinates, sorbitan monooleate, and polyisobutylene succinic anhydrides.

The corrosion control composition can further include a paraffin inhibitor. The composition comprises from about 0.1% to about 10%, from about 0.1% to about 5%, or from about 0.5% to about 4% by weight of paraffin, based on the total weight of the composition. An inhibitor may be included. Suitable paraffin inhibitors include, but are not limited to, paraffin crystal modifiers and dispersant/crystal modifier combinations. Suitable paraffin crystal modifiers include alkyl acrylate copolymers, alkyl acrylate vinyl pyridine copolymers, ethylene vinyl acetate copolymers, maleic anhydride copolymers, branched polyethylenes, naphthalenes, anthracenes, microcrystalline waxes, and/or asphaltenes. , but not limited to. Suitable paraffin dispersants include, but are not limited to, dodecylbenzene sulfonate, oxyalkylated alkylphenols, and oxyalkylated alkylphenol resins.

The corrosion control composition can further include a scale inhibitor. The composition comprises from about 0.1% to about 20%, from about 0.5% to about 10%, or from about 1% to about 10% by weight of a scale inhibitor, based on the total weight of the composition. can include Suitable scale inhibitors include phosphates, phosphate esters, phosphoric acid, phosphonates, phosphonic acids, polyacrylamides, salts of acrylamidomethylpropanesulfonate/acrylic acid copolymer (AMPS/AA), phosphorylated maleic acid copolymers. (PHOS/MA), mono-, bis-, and oligomeric phosphinosuccinic acid (PSO) derivatives, polycarboxylic acids, hydrophobically modified polycarboxylic acids, and polymaleic acid/acrylic acid/acrylamidomethylpropanesulfonate terpolymers (PMA/AA/ AMPS), but are not limited to these.

The corrosion control composition can further include an emulsifier. The composition may contain from about 0.1% to about 10%, from about 0.5% to about 5%, or from about 0.5% to about 4% by weight of an emulsifier, based on the total weight of the composition. can include Suitable emulsifiers include salts of carboxylic acids, products of acylation reactions between carboxylic acids or carboxylic acid anhydrides and amines, and alkyl, acyl, and amide derivatives of sugars (alkyl-sugar emulsifiers). but not limited to these.

The corrosion control composition can further include a water purification agent. The composition contains from about 0.1% to about 10%, from about 0.5% to about 5%, or from about 0.5% to about 4% water, based on the total weight of the composition. Detergents may be included. Suitable water purification agents include inorganic metal salts such as alum, aluminum chloride, and aluminum chlorohydrate, or acrylic acid-based polymers, acrylamide-based polymers, polymerized amines, alkanolamines, thiocarbamates, and diallyldimethylammonium chloride (DADMAC). ), including but not limited to organic polymers such as cationic polymers such as

The corrosion control composition can further include an emulsion breaker. The composition comprises from about 0.1% to about 10%, from about 0.5% to about 5%, or from about 0.5% to about 4% by weight of the emulsion, based on the total weight of the composition. Disrupting agents can be included. Suitable emulsion-breaking agents include, but are not limited to, dodecylbenzylsulfonic acid (DDBSA), sodium salt of xylenesulfonic acid (NAXSA), epoxidized and propoxylated compounds, and resins such as phenolic and epoxy resins. not.

The corrosion control composition can further include a hydrogen sulfide scavenger. The composition contains from about 1% to about 50%, from about 1% to about 40%, from about 1% to about 30%, from about 0.1% to about 10 wt%, about 0.5 wt% to about 5 wt%, or about 0.5 wt% to about 4 wt% hydrogen sulfide scavenger can be included. Suitable additional hydrogen sulfide scavengers include oxidizing agents (e.g. inorganic peroxides such as sodium peroxide or chlorine dioxide), aldehydes (e.g. formaldehyde, glyoxal, glutaraldehyde, acrolein or methacrolein). 1-10), triazines (such as monoethanolamine triazine, monomethylamine triazine, and triazines from multiple amines, or mixtures thereof), condensation products of secondary or tertiary amines and aldehydes, and alkyl Examples include, but are not limited to, condensation products of alcohols and aldehydes.

The corrosion control composition can further include a gas hydrate inhibitor. The composition contains about 0.1% to about 25%, about 0.5% to about 20%, about 1% to about 10%, about 0.1% to about 25%, about 0.5% to about 20%, about 1% to about 10%, by weight based on the total weight of the composition. % to about 10%, from about 0.5% to about 5%, or from about 0.5% to about 4% by weight of gas hydrate inhibitor. Suitable gas hydrate inhibitors include, but are not limited to, thermodynamic hydrate inhibitors (THI), kinetic hydrate inhibitors (KHI), and agglomeration inhibitors (AA). Suitable thermodynamic hydrate inhibitors include sodium chloride, potassium chloride, calcium chloride, magnesium chloride, sodium bromide, formate brine (e.g. potassium formate), polyols (glucose, sucrose, fructose, maltose, lactose, glucone acid salts, monoethylene glycol, diethylene glycol, triethylene glycol, monopropylene glycol, dipropylene glycol, tripropylene glycol, tetrapropylene glycol, monobutylene glycol, dibutylene glycol, tributylene glycol, glycerol, diglycerol, triglycerol, and sugar alcohols (e.g., sorbitol, mannitol), methanol, propanol, ethanol, glycol ethers (diethylene glycol monomethyl ether, ethylene glycol monobutyl ether, etc.), and alkyl or cyclic esters of alcohols (ethyl lactate, butyl lactate, methyl benzoate) ethyl, etc.), but are not limited to these.

The corrosion control composition can further include a dynamic hydrate inhibitor. The composition contains about 0.1% to about 25%, about 0.5% to about 20%, about 1% to about 10%, about 0.1% to about 25%, about 0.5% to about 20%, about 1% to about 10%, by weight based on the total weight of the composition. % to about 10%, from about 0.5% to about 5%, or from about 0.5% to about 4% by weight of dynamic hydrate inhibitor. Suitable dynamic hydrate and aggregation inhibitors include polymers and copolymers, polysaccharides (such as hydroxyethylcellulose (HEC), carboxymethylcellulose (CMC), starch, starch derivatives, and xanthan), lactams (polyvinylcaprolactam, polyvinyl lactams, etc.), pyrrolidones (including polyvinylpyrrolidones of various molecular weights), fatty acid salts, ethoxylated alcohols, propoxylated alcohols, sorbitan esters, ethoxylated sorbitan esters, polyglycerol esters of fatty acids, alkyl glucosides, alkyl polyglucosides, alkyl sulfates. , alkylsulfonates, alkylestersulfonates, alkylaromatic sulfonates, alkylbetaines, alkylamidobetaines, hydrocarbon dispersants (lignosulfonates, iminodisuccinates, polyaspartates, etc.), amino acids, and proteins, but these is not limited to

The corrosion control composition can further include a pH modifier. The composition has a pH of from about 0.1% to about 20%, from about 0.5% to about 10%, or from about 0.5% to about 5%, by weight based on the total weight of the composition. Modifiers can be included. Suitable pH adjusters include alkali hydroxides, alkali carbonates, alkali bicarbonates, alkaline earth metal hydroxides, alkaline earth metal carbonates, alkaline earth metal bicarbonates, and mixtures or combinations thereof. including but not limited to. Exemplary pH adjusters include sodium hydroxide, potassium hydroxide, calcium hydroxide, calcium oxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, magnesium oxide, and magnesium hydroxide.

The corrosion control composition can further include a surfactant. The composition contains from about 0.1% to about 10%, from about 0.5% to about 5%, or from about 0.5% to about 4% by weight of the interfacial surface based on the total weight of the composition. It can contain an active agent. Suitable surfactants can be nonionic, semi-nonionic, cationic, anionic, amphoteric, zwitterionic, gemini, dicationic, dianionic surfactants, or mixtures thereof. Anionic surfactants include alkyl aryl sulfonates, olefin sulfonates, paraffin sulfonates, alcohol sulfates, alcohol ether sulfates, alkyl carboxylates and alkyl ether carboxylates, as well as alkyl and ethoxylated alkyl phosphates, and mono- and dialkyl sulfosuccinates. sulfosuccinates and sulfosuccinates. Nonionic surfactants include alcohol alkoxylates, alkylphenol alkoxylates, block copolymers of ethylene, block copolymers of ethylene and propylene, propylene and butylene oxides, alkyldimethylamine oxides, alkyl-bis(2-hydroxyethyl)amine oxides. , alkylamidopropyldimethylamine oxides, alkylamidopropyl-bis(2-hydroxyethyl)amine oxides, alkylpolyglucosides, polyalkoxylated glycerides, sorbitan esters and polyalkoxylated sorbitan esters, and alkoyl polyethylene glycol esters and diesters. be done. Also included are betaines and sultanes, amphoteric surfactants such as alkylamphoacetates and amphodiacetates, alkylamphopropionates and amphodipropionates, and alkyliminodipropionates.

In some embodiments, the surfactant is a phosphate ester of an ethoxylated C10-C16 alcohol, an ethoxylated C11-C14 iso- or C13-rich phosphate, an ethoxylated nonylphenol, an ethoxylated branched-chain nonylphenol, or mixtures thereof. be.

The corrosion control composition can further comprise other additional corrosion control composition agents that provide functional and/or beneficial properties. For example, additional corrosion control composition agents may include sequestering agents, solubilizers, lubricants, buffers, detergents, rinse aids, preservatives, binders, thickeners or other viscosity modifiers, processing agents. Auxiliaries, water conditioners, foam control agents or foam generators, ion deposition inhibitors or systems, aesthetic improvers (e.g., dyes, odorants, perfumes), or others suitable for combination with the corrosion inhibitor composition. and mixtures thereof. Additional agents will vary according to the particular corrosion control composition being manufactured and its intended use, as will be appreciated by those skilled in the art.

Alternatively, the corrosion control composition does not contain or contain any of the additional corrosion control composition agents.

Additionally, the corrosion control composition can be formulated into exemplary compositions comprising the following components, as shown in Table 1 below. These formulations contain a range of listed ingredients and can optionally contain additional agents. The values in Table 1 below are weight percentages.

Water-Based Corrosion Control Compositions or their use solutions are applied to water-based systems to prevent corrosion on or to surfaces in water-based systems. In some embodiments, the water system in the methods disclosed herein is an industrial water system. In other embodiments, water systems include cooling water systems including open recirculating systems, closed and once-through cooling water systems, boiler and boiler water systems, oil well systems, downhole formations, geothermal wells and other water systems in oil and gas operations. , mineral washing systems, flotation and charity systems, paper mill digesters, washers, bleaching plants, stock chests, white water systems, paper machine surfaces, black liquor evaporators in the pulp industry, gas scrubbers and air washers, continuous casting processes in the metallurgical industry, Air conditioning and refrigeration systems, industrial and petroleum process waters, indirect contact cooling and heating waters, water recycling systems, water purification systems, membrane filtration systems, food processing streams (meat, vegetables, sugar beets, sugar cane, grains, poultry meat, fruit , and soybeans), waste treatment systems, sanitizers, liquid-solid applications, municipal sewage treatment, municipal water systems, drinking water systems, aquifers, reservoirs, sprinkler systems, and water heaters. .

Aqueous systems can be those used in oil and gas operations. Aqueous systems can include water, oils, and solids. In some embodiments, the aqueous system comprises mostly oils or hydrocarbons. For example, water systems include oil or gasoline in tanks or pipelines. In some embodiments, the water system is one used in oil and gas operations.

In some embodiments, the water system is a cooling water system, including open recirculating, closed and once-through cooling water systems, paper machine surfaces, food processing streams, waste treatment systems, or drinking water systems.

Uses of Disclosed Methods or Compositions In some embodiments, with respect to the methods disclosed herein, providing a corrosion control composition to an aqueous system comprises a corrosion control composition, one or more dicationic or Means that the dianionic compound, or its use solution, is added in a water-containing fluid or onto a water-based surface. In other embodiments, providing the corrosion control composition to the water system means adding the corrosion control composition or the dicationic or dianionic compound onto the surface or into the water of the water system. In some other embodiments, providing the corrosion control composition to the aqueous system comprises adding the corrosion control composition, the dicationic or dianionic compound, or their use solution to a fluid or gas contacting the surface of the aqueous system. means to The corrosion control composition, dicationic or dianionic compound, or use solution thereof may be added continuously or intermittently when more compound or composition may be required.

A corrosion control composition or use solution of one or more dicationic or dianionic compounds, as used herein, refers to a diluted solution of the composition or compound in a diluent. Diluent, as used herein, refers to one of water, aqueous water, or a carrier or solvent as defined herein. The corrosion control composition or compound may be used at 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 to 1,000,000 times, or any value therebetween. It can be diluted to form a use solution, which can then be provided on an aqueous system or surface. In this disclosure, when a composition or a dicationic or dianionic compound is applied, either the composition/compound or its use solution is applied.

In some embodiments, the corrosion control compositions or dicationic or dianionic compounds disclosed herein are used such that the concentration of the composition or compound in the treated water system is from about 1 ppm to about 1000 ppm. , can be added to the water of an aqueous system. In other embodiments, the amount of corrosion control composition or dicationic or dianionic compound in the water of an aqueous system is about 5 ppm to about 100 ppm, about 5 ppm to about 50 ppm, about 5 ppm to about 40 ppm, about 5 ppm to about 30 ppm, about in the range of 10 ppm to about 60 ppm, about 10 ppm to about 50 ppm, about 10 ppm to about 40 ppm, about 10 ppm to about 30 ppm, about 20 ppm to about 60 ppm, about 20 ppm to about 50 ppm, about 20 ppm to about 40 ppm, or about 20 ppm to about 30 ppm could be. In some embodiments, the corrosion control composition or dicationic or dianionic compound is water-soluble to an amount ranging from about 100 ppm to about 1000 ppm, from about 125 ppm to about 1000 ppm, from about 250 ppm to about 1000 ppm, or from about 500 ppm to about 1000 ppm. can be added to

The corrosion control compositions or dicationic or dianionic compounds are used for corrosion control in oil and gas applications, such as by treating gas or liquid streams with an effective amount of the compounds or compositions described herein. obtain. The compounds and compositions can be used in any industry where it is desirable to prevent corrosion on surfaces.

The corrosion control composition or dicationic or dianionic compound can be used in condensate/oil/gas systems, or any combination thereof. For example, corrosion control compositions or dicationic or dianionic compounds can be used to control corrosion on heat exchanger surfaces. The corrosion control composition or dicationic or dianionic compound can be applied to gases or liquids produced or used in the production, transportation, storage and/or separation of crude oil or natural gas. The corrosion control composition or dicationic or dianionic compound can be applied to gas streams used or produced in coal-burning processes, such as coal-fired power plants.

Corrosion control compositions or dicationic or dianionic compounds are applied to gases or liquids produced or used in wastewater processes, farms, abattoirs, landfills, municipal wastewater plants, coking coal processes, or biofuel processes. obtain.

The fluid into which the corrosion control composition or dicationic or dianionic compound can be introduced can be an aqueous medium. Aqueous media may include water, gases, and optionally liquid hydrocarbons.

The fluid into which the corrosion control composition or dicationic or dianionic compound can be introduced can be a liquid hydrocarbon. Liquid hydrocarbons include crude oil, heavy oil, processed residue, bituminous oil, coker oil, coker gas oil, fluid catalytic cracking feedstocks, gas oil, naphtha, fluid catalytic cracking slurry, diesel fuel, fuel oil, jet fuel, gasoline, and kerosene. can be any type of liquid hydrocarbon, including, but not limited to, The fluid or gas can be a refined hydrocarbon product.

The liquid or gas treated with the corrosion control composition or dicationic or dianionic compound can be at any selected temperature, such as ambient temperature or elevated temperature. The fluid (eg, liquid hydrocarbon) or gas can be at a temperature of about 40°C to about 250°C. The fluid or gas can be at a temperature of about -50°C to about 300°C, about 0°C to about 200°C, about 10°C to about 100°C, or about 20°C to about 90°C. The fluid or gas is about 22°C, about 23°C, about 24°C, about 25°C, about 26°C, about 27°C, about 28°C, about 29°C, about 30°C, about 31°C, about 32°C, about 33°C, about 34°C, about 35°C, about 36°C, about 37°C, about 38°C, about 39°C, or about 40°C can be at a temperature of The fluid or gas is about The temperature can be 94°C, about 95°C, about 96°C, about 97°C, about 98°C, about 99°C, or about 100°C.

The corrosion control composition or dicationic or dianionic compound can be added to the fluid (or water system) at varying levels of moisture content. For example, the moisture content can be 0% to 100% volume/volume (v/v), 1% to 80% v/v, or 1% to 60% v/v. The fluid can be an aqueous medium containing varying levels of salinity. The fluid can have a total dissolved solids (TDS) salinity of 0% to 25%, about 1% to 24%, or about 10% to 25% weight/weight (w/w).

The aqueous fluid or gas or aqueous water into which the corrosion control composition or dicationic or dianionic compound is introduced can be contained in and/or exposed to many types of equipment. For example, a fluid or gas can be contained in a device that transports the fluid or gas from one point to another, such as an oil and/or gas pipeline. The device may be part of an oil and/or gas refinery such as a pipeline, separation vessel, dehydrator, or gas line. Fluids may be contained in and/or exposed to equipment used in petroleum extraction and/or production, such as wellheads. The device may be part of a coal-fired power plant. The device can be a scrubber such as a wet flue gas desulfurizer, a spray drying absorber, a dry sorbent injector, a spray tower, a contact tower or a bubble tower. The device can be a cargo ship, a storage vessel, a storage tank, or a pipeline connecting tanks, ships, or processing units.

The corrosion control composition or dicationic or dianionic compound can be introduced into the water-based fluid or gas by any suitable method to ensure dispersion through the fluid or gas. For example, the corrosion control composition or dicationic or dianionic compound can be added to the hydrocarbon fluid before it contacts the surface.

The corrosion control composition or dicationic or dianionic compound can be added at a point in the flow line upstream from the point where corrosion control is desired. For example, the corrosion control composition or dicationic or dianionic compound can be injected using mechanical devices such as chemical injection pumps, pipe tees, injection fittings, atomizers, quills, and the like.

Corrosion control compositions or dicationic or dianionic compounds can be fed into oil and/or gas pipelines using umbilical lines. A capillary injection system may be used to deliver the corrosion control composition or dicationic or dianionic compound to the selected fluid.

The fluid into which the corrosion control composition or dicationic or dianionic compound can be introduced can be an aqueous medium. Aqueous media may include water, gases, and optionally liquid hydrocarbons. The fluid into which the corrosion control composition or dicationic or dianionic compound can be introduced can be a liquid hydrocarbon.

The corrosion control composition or dicationic or dianionic compound can be introduced into liquids and mixtures of some liquids, liquids and gases, liquids, solids and gases. The corrosion control composition or dicationic or dianionic compound can be injected into the gas stream as an aqueous or non-aqueous solution, mixture, or slurry.

A fluid or gas can be passed through an absorber tower containing a corrosion control composition or a dicationic or dianionic compound.

Corrosion control compositions or dicationic or dianionic compounds can be applied to fluids or gases to provide any selected concentration. In practice, the corrosion control composition or dicationic or dianionic compound is typically added to the flowline to provide from about 0.01 ppm to about 5,000 ppm of the corrosion control composition or dicationic or dianionic compound. provides an effective treatment input of The corrosion control composition or dicationic or dianionic compound is applied to a fluid or gas at a concentration of about 1 parts per million (ppm) to about 1,000,000 ppm, about 1 parts per million (ppm) to about 100 ,000 ppm, or from about 10 ppm to about 75,000 ppm. The polymer salt/composition can be applied to a fluid to provide an active agent concentration of about 100 ppm to about 10,000 ppm, about 200 ppm to about 8,000 ppm, or about 500 ppm to about 6,000 ppm. Active substance concentration means the concentration of the corrosion control composition or the dicationic or dianionic compound.

The corrosion control composition or dicationic or dianionic compound is applied to a fluid or gas to provide about 0.1 ppm, about 0.5 ppm, about 1 ppm, about Active concentrations of 2 ppm, about 5 ppm, about 10 ppm, about 20 ppm, about 100 ppm, about 200 ppm, about 500 ppm, or about 1,000 ppm can be provided. The corrosion control composition or dicationic or dianionic compound is applied to a fluid or gas or water system to provide about 0.125 ppm, about 0.25 ppm, about 0.625 ppm, about 1 ppm in the treated fluid, gas or water system. , about 1.25 ppm, about 2.5 ppm, about 5 ppm, about 10 ppm, or about 20 ppm active agent concentration. Each water system can have its own dosage level requirements, and the effective dosage level of corrosion control composition or dicationic or dianionic compound to sufficiently reduce the growth rate of microorganisms or biofilms depends on it. may vary depending on the water system used.

The corrosion control composition or dicationic or dianionic compound can be applied continuously, batchwise, or combinations thereof. Dosing of the corrosion control composition or dicationic or dianionic compound can be continuous. Administration of the corrosion control composition or dicationic or dianionic compound can be intermittent (eg, batch processing) or can be continuous/sustained and/or intermittent.

Dosage rates for continuous processing typically range from about 10 to about 500 ppm, or from about 10 to about 200 ppm. Dosage rates for batch processing typically range from about 10 to about 400,000 ppm, or from about 10 to about 20,000 ppm. The corrosion control composition or dicationic or dianionic compound can be applied as a tablet to the pipeline to provide a high dosage (eg, 20,000 ppm) composition.

Flow lines in which the corrosion control composition or dicationic or dianionic compound is used have a flow rate of from about 0.1 ft/sec to about 1,000 ft/sec, or from about 0.1 ft/sec to about 50 ft/sec. can be seconds. The corrosion control composition or dicationic or dianionic compound can also be formulated with water to facilitate addition to the flowline.

An aqueous surface can be any surface that can come into contact with aqueous water or water vapor in some way. The surface may be part of a well or apparatus used for the production, transport, storage, and/or separation of fluids such as crude oil or natural gas.

More specifically, the surface can be part of equipment that uses coal burning processes, wastewater processes, farms, slaughterhouses, landfills, municipal wastewater plants, coking coal processes, or biofuel processes. Preferably, the surface may be part of a device used in the production of crude oil or natural gas.

The apparatus can include pipelines, storage vessels, downhole injection tubes, flowlines, or injection lines.

Corrosion control compositions or dicationic or dianionic compounds are useful for inhibiting corrosion of containers, processing facilities, or equipment in the food service or food processing industry. Corrosion control compositions or dicationic or dianionic compounds are of particular value for use on food packaging materials and equipment, especially for cold or hot aseptic packaging. Examples of processing equipment in which the corrosion control compositions or dicationic or dianionic compounds may be used include food processing lines such as milk line dairy, continuous brewing systems, pumpable food systems and beverage lines, dishwashers, low temperature. Processing equipment such as dishwashers, tableware, bottle washers, bottle chillers, warmers, 3rd sink washers, tanks, vats, lines, pumps and hoses (e.g. milk, cheese, ice cream, and dairy processing equipment for processing other dairy products), and transportation vehicles. Corrosion control compositions or dicationic or dianionic compounds can be used to control corrosion in tanks, lines, pumps, and other equipment used in the manufacture and storage of soft drink ingredients, and in beverage bottling. Or it can also be used for containers.

Corrosion control compositions or dicationic or dianionic compounds are also used on or in other industrial equipment and in other industrial process streams such as heaters, cooling towers, boilers, retort water, rinse water, sterile packaging wash water, and the like. can be The corrosion control composition or dicationic or dianionic compound can be used to treat recreational water surfaces such as pools, spas, recreational water chutes and slides, fountains and the like.

Corrosion control compositions or dicationic or dianionic compounds are used to treat metal surfaces in contact with cleaning agents in surfaces found in cleaning and/or housekeeping applications, food processing equipment and/or plant applications, and laundry applications. can be used for For example, washing machines such as tunnel washing machines for washing fabrics can be treated according to the methods disclosed herein.

The corrosion control compositions or dicationic or dianionic compounds may be used or applied in combination with low temperature dish and/or dishwashing disinfectant final rinses, toilet bowl cleaners, and laundry bleaches. The corrosion control composition or dicationic or dianionic compound can be used to treat metal surfaces such as tableware that have been cleaned and/or sanitized with a source of corrosion.

The corrosion control composition or dicationic or dianionic compound can be dispensed by any suitable method commonly known to those of ordinary skill in the art. For example, a spray-type dispenser can be used. A spray-type dispenser impinges a water spray on an exposed surface of the composition to dissolve a portion of the composition, and then immediately directs a concentrate solution containing the composition from the dispenser to a storage reservoir or directly to the point of use. Function.

The corrosion control composition or dicationic or dianionic compound can be dispensed by intermittent or continuous immersion in aqueous water, fluid, or gas. The corrosion control composition or dicationic or dianionic compound can then dissolve, for example, at a controlled or predetermined rate. This rate can be effective in maintaining a concentration of dissolved compound or composition that is effective for use in accordance with the methods disclosed herein.

The corrosion control compositions disclosed herein comprise from about 10% to about 90% by weight of a carrier, a biocide, additional corrosion inhibitors, additional corrosion control composition agents, or combinations thereof, and about 10% to about 90% by weight of one or more dicationic or dianionic compounds, about 20% to about 80% by weight of carrier, biocide, additional corrosion inhibitor, additional corrosion control composition agent, or combinations thereof, and from about 20% to about 80% by weight of one or more dicationic or dianionic compounds, from about 30% to about 70% by weight of a carrier, a biocide, an additional corrosion inhibitor, additional or a combination thereof, and from about 30% to about 70% by weight of one or more dicationic or dianionic compounds, or from about 40% to about 60% by weight of a carrier, a biocide. , additional corrosion inhibitors, additional corrosion control composition agents, or combinations thereof, and from about 40 to about 60 weight percent of one or more dicationic or dianionic compounds.

As used herein, the terms "substantially free" or "free" are either completely devoid of that component or have such a small amount of that component that it does not affect the performance of the composition. Refers to composition. Components may be present as impurities or as contaminants and should be less than 0.5% by weight. In another embodiment, the amount of component is less than 0.1 wt%, and in yet another embodiment, the amount of component is less than 0.01 wt%.

The terms "weight percent", "wt-%", "percent by weight", "% by weight" and variations thereof are used herein to When used, it refers to the concentration of a substance divided by the total weight of the composition multiplied by 100. It is understood that, as used herein, "percent," "%," etc. are intended to be synonymous with "weight percent," "weight percent," and the like.

Embodiments of the invention are further defined in the following non-limiting examples. It should be understood that these Examples, while indicating specific embodiments of the invention, are given by way of illustration only. From the above discussion and these examples, one skilled in the art can ascertain the essential features of this invention, and without departing from its spirit and scope, it can be adapted to various usages and conditions. Various changes and modifications of the embodiments of the invention may be made. Accordingly, various modifications of the embodiments of the invention, in addition to those shown and described herein, will become apparent to those skilled in the art from the foregoing description. Such modifications are also intended to fall within the scope of the appended claims.

Example 1
General scheme for synthesizing exemplary dicationic compounds containing two quaternary groups:
An exemplary dicationic compound containing two quaternary groups disclosed herein is a primary amine (1 mole) and an α,β-unsaturated carbonyl compound containing at least one quaternary group (at least two mol) by an azamichael addition reaction. A general synthetic reaction scheme for the preparation of the disclosed dicationic surfactants is shown in FIG.

In FIG. 2, R ¹¹ is R ¹ or R ¹ -Z-(CH ₂ ) _m -, and R ¹ is unsubstituted or substituted straight or branched chain C ₁ -C ₃₀ alkyl, cyclic alkyl, alkenyl , or an alkynyl group, Z is NH or O, R ² is H, CH ₃ , or an unsubstituted straight or branched C ₂ -C ₁₀ alkyl, alkenyl, or alkynyl group, m is an integer of 1-4, and n is an integer of 1-20.

The reaction shown in Figure 2 can be carried out in water at 80 ^° C. The progress of this reaction is monitored for monomer consumption by ESI-MS and/or NMR spectroscopy. The reaction is typically stopped when about a 98% yield of diquat product is obtained. The synthesized compounds of the following examples were made according to this scheme, except that the reactants were different in each of the examples as detailed in each example.

Example 2
Synthesis of 3,3′-((3,3′-(octylazanediyl)bis(propanoyl))bis(azanediyl))bis(N,N,N-trimethylpropane-1-aminium) chloride (I)
In this example, (3-acrylamidopropyl)trimethylammonium chloride (APTAC, 75%, 30 grams, 0.10 mol) was added to a 250 mL three-neck round bottom flask (RBF) equipped with an overhead stirrer, temperature probe, and condenser. filled. Benzyltrimethylammonium hydroxide (0.9 grams, 10%, 0.0005 mol) and water (41 g) were added to the flask. Octylamine (7 grams, 99%, 0.053 mol) was then added in portions to the well-stirred reaction mixture. The resulting suspension was stirred at 80° C. overnight. Upon completion of the reaction, the suspension turned into a clear yellowish solution. Diquat compound, 3,3′-((3,3′-(octylazanediyl)bis(propanoyl))bis(azanediyl))bis(N,N,N-trimethylpropane-1-aminium) chloride (compound I and ) was stored in a container. Mass spectrometry (+ESI-MS) confirmed the synthesis of dicationic compound I: calculated [M-2Cl ^- ] ²⁺ 235.73, found 235.7241; calculated [M-Cl ^- ] ⁺ 506. 42, found 506.4182.

Example 3
Synthesis of 3,3′-((3,3′-(dodecylazanediyl)bis(propanoyl))bis(azanediyl))bis(N,N,N-trimethylpropane-1-aminium) chloride (II)
In this example, (3-acrylamidopropyl)trimethylammonium chloride (APTAC, 75%, 30 grams, 0.10 mol) was charged to a 250 mL RBF equipped with an overhead stirrer, temperature probe, and condenser. Benzyltrimethylammonium hydroxide (0.9 grams, 10%, 0.0005 mol) and water (63 g) were added to the flask. Dodecylamine (10 grams, 98%, 0.053 mol) was then added portionwise to the well-stirred reaction mixture. The resulting suspension was stirred at 80° C. overnight. Upon completion of the reaction, the suspension turned into a clear yellowish solution. diquat compound, 3,3′-((3,3′-(dodecylazanediyl)bis(propanoyl))bis(azanediyl))bis(N,N,N-trimethylpropane-1-aminium) chloride (compound II and The resulting aqueous solution (approximately 31 wt. Mass spectrometry (+ESI-MS) confirmed the synthesis of diquat compound (II): calculated [M-2Cl ^- ] ²⁺ 263.76, found 263.7554; calculated [M-Cl ^- ] ⁺ 562. .48, found 562.4806.

Example 4
Synthesis of 3,3′-((3,3′-(hexadecylazanediyl)bis(propanoyl))bis(azanediyl))bis(N,N,N-trimethylpropane-1-aminium) chloride (III)
In this example, (3-acrylamidopropyl)trimethylammonium chloride (APTAC, 75%, 41 grams, 0.149 mol) was charged to a 250 mL RBF equipped with an overhead stirrer, temperature probe, and condenser. Benzyltrimethylammonium hydroxide (0.9 grams, 10%, 0.0005 mol) and water (100 g) were added to the flask. Hexadecylamine (20 grams, 90%, 0.0745 mol) was then added portionwise to the well-stirred reaction mixture. The resulting suspension was stirred at 80° C. overnight. Upon completion of the reaction, the suspension turned into a clear yellowish solution. The resulting diquat compound, 3,3′-((3,3′-(hexadecylazanediyl)bis(propanoyl))bis(azanediyl))bis(N,N,N-trimethylpropane-1-aminium) chloride (designated compound III) in water (about 30% by weight) was used as received. Mass spectrometry (+ESI/MS) confirmed the synthesis of diquat compound (III): calculated [M−2Cl ⁻ ] ²⁺ 291.79, found 291.7870; calculated [M−Cl ⁻ ] ⁺ 618. .54, found 618.5439.

Example 5
Synthesis of 3,3′-((3,3′-(octylazanediyl)bis(propanoyl))bis(azanediyl))bis(N,N,N-trimethylpropane-1-aminium) chloride (IV)
In this example, (3-acrylamidopropyl)trimethylammonium chloride (APTAC, 75%, 40 grams, 0.145 mol) was charged to a 250 mL RBF equipped with an overhead stirrer, temperature probe, and condenser. Benzyltrimethylammonium hydroxide (0.9 grams, 10%, 0.0005 mol) and water (100 g) were added to the flask. Octadecylamine (20 grams, 98%, 0.072 mol) was then added in portions to the well-stirred reaction mixture. The resulting suspension was stirred at 80° C. overnight. Upon completion of the reaction, the suspension turned into a clear yellowish solution. diquat compound, 3,3′-((3,3′-(octylazanediyl)bis(propanoyl))bis(azanediyl))bis(N,N,N-trimethylpropane-1-aminium) chloride (compound IV and The resulting aqueous solution (approximately 31 wt. Mass spectrometry (+ESI-MS) confirmed the synthesis of diquat compound IV: calculated [M-2Cl ^- ] ²⁺ 305.80, found 305.8014; calculated [M-Cl ^- ] ⁺ 646.58. , found 648.5791.

Example 6
3,3′-((3,3′-(octadecan-9-en-1-ylazanediyl)bis(propanoyl))bis(azanediyl))bis(N,N,N-trimethylpropane-1-aminium) chloride Synthesis (V)
In this example, (3-acrylamidopropyl)trimethylammonium chloride (APTAC, 75%, 30 grams, 0.109 mol) was charged to a 250 mL RBF equipped with an overhead stirrer, temperature probe, and condenser. Benzyltrimethylammonium hydroxide (0.25 grams, 10%, 0.0001 mol) and water (70 g) were added to the flask. Oleylamine (15 grams, 95%, 0.053 mol) was then added in portions to the well-stirred reaction mixture. The resulting suspension was stirred at 80° C. overnight. Upon completion of the reaction, the suspension turned into a clear yellowish solution. Diquat compound, 3,3′-((3,3′-(octadeca-9-en-1-ylazanediyl)bis(propanoyl))bis(azanediyl))bis(N,N,N-trimethylpropane-1-aminium ) The resulting aqueous solution (approximately 32% by weight) of chloride (designated V) was used as is. Mass spectrometry (+ESI-MS) confirmed the synthesis of the diquat compound: calculated [M-2Cl ^- ] ²⁺ 304.80, found 304.7949; calculated [M-Cl ^- ] ⁺ 644.56, Actual value 644.5596.

Example 7
3,3′-((3,3′-((3-octadeca-9-en-1-ylamino)propyl)azanediyl)bis(propanoyl))bis(azanediyl))bis(N,N,N-trimethylpropane -1-Aminium) chloride synthesis (VI)
In this example, (3-acrylamidopropyl)trimethylammonium chloride (APTAC, 75%, 42 grams, 0.152 mol) was charged to a 250 mL RBF equipped with an overhead stirrer, temperature probe, and condenser. Benzyltrimethylammonium hydroxide (0.25 grams, 10%, 0.0001 mol) and water (130 g) were added to the flask. N-oleylpropanediamine (25 grams, 99%, 0.076 mol) was then added portionwise to the well-stirred reaction mixture. The resulting suspension was stirred at 80° C. overnight. Upon completion of the reaction, the suspension turned into a clear yellowish solution. Diquat compound, 3,3′-((3,3′-((3-octadecan-9-en-1-ylamino)propyl)azanediyl)bis(propanoyl))bis(azanediyl))bis(N,N,N -trimethylpropane-1-aminium) chloride (referred to as VI) was used as is. Mass spectrometry (+ESI/MS) confirmed the synthesis of diquat compound VI: calculated [M−2Cl ⁻ ] ²⁺ 333.32, found 333.3238; calculated [M−Cl ⁻ ] ⁺ 701.62. , found 701.6173.

Example 8
Surface Tension Measurements Surface tension measurements were performed on a Tracker tensiometer (Teclis Instruments) at room temperature. Various solutions with different concentrations of the exemplary dicationic compounds were prepared and surface tension measurements were performed. Surface tension as a function of concentration for exemplary dicationic compounds was measured and listed in Table 2.

Example 9
Corrosion Control Effectiveness of Some Exemplary dicationic Compounds In this example, several exemplary dicationic compounds were tested for their effectiveness in inhibiting corrosion. The samples tested were made according to the reactions presented in Example 1 and listed in Table 3 below. The precursor primary amine for each compound is listed and the other reactant that produces the listed samples is (3-acrylamidopropyl)trimethylammonium chloride.

Corrosion control effectiveness is typically measured by the Corrosion Bubble Cell Test. The bubble test simulates a low flow region where little or no mixing of water and oil occurs. This test was conducted in a fluid containing 80% brine (3% sodium chloride) and 20% hydrocarbons (75% LVT-200 and 25% xylene). The fluid was placed in a kettle and purged with carbon dioxide. Brine was added to the kettle and purged with carbon dioxide. The brine was continuously purged with carbon dioxide to saturate the brine before starting the test. After the start of the test, the test cell was blanketed with carbon dioxide to maintain saturation for 1 hour before inserting the electrodes and throughout the test. The kettle was agitated at 150 revolutions per minute (rpm) for the duration of the test to maintain thermal equilibrium at 80°C. Corrosion rates were measured by the Linear Polarization Resistance (LPR) technique. The working electrode used was 1018 carbon steel. Both the counter and reference electrodes were Hastelloy. All electrodes were cleaned and polished prior to testing. 20 ppm of each of the compositions (2 ppm of each of the various dicationic compounds or their salts as synergists in organic solvents, or the control C ₁₂ -C ₁₈ alkyldimethylbenzylammonium chloride and 1% 2-mercaptoethanol ( 2ME)) were loaded into their respective cells and data were collected for 3 hours. Data were collected overnight.

The reference compounds in this example are the commonly used benzylammonium chloride quaternary and imidazoline chemicals, respectively.

The results of the bubble test are shown in Figure 3 and Table 3, where ppm is parts per million, CI is corrosion inhibitor, and mpy is mils/year. 0.2 ppm of 2-mercaptoethanol (2ME) was present with each dicationic compound tested or control. FIG. 3 shows the corrosion rate in mils/year during the bubble test period (18 hours). No 2-mercaptoethanol (2ME) was added to blank samples.

Whilst the invention has been thus described, it will be apparent that it can be varied in many ways. Such variations are not to be regarded as a departure from the spirit and scope of this disclosure, and all such modifications are intended to be included within the scope of the following claims.

式中、
Ｘが、ＮＨまたはＯであり、
Ｒ^１１が、Ｒ^１またはＲ^１－Ｚ－（ＣＨ_２）_ｍ－であり、
Ｒ^１が、非置換もしくは置換の直鎖もしくは分岐鎖Ｃ_１～Ｃ_３０アルキル、環状アルキル、アルケニル、またはアルキニル基であり、
Ｚが、ＮＨまたはＯであり、
Ｒ^２が、Ｈ、ＣＨ_３、または非置換の直鎖もしくは分岐鎖Ｃ_２～Ｃ_１０アルキル、アルケニル、もしくはアルキニル基であり、
ｍが、１～４の整数であり、
Ｒ^３が、存在しないか、または非置換の直鎖Ｃ_{１～Ｃ３０}アルキレン基であり、
Ｙが、－ＮＲ^４Ｒ^５Ｒ^６（＋）、またはその塩であり、
Ｒ^４、Ｒ^５、およびＲ^６が独立して、Ｃ_１～Ｃ_１０アルキル基である、化合物。
［２］
ＸがＮＨである、項目１に記載の化合物。
［３］
ＸがＯである、項目１に記載の化合物。
［４］
Ｒ^１１がＲ^１である、項目１～３のいずれか一項に記載の化合物。
［５］
Ｒ^１１が、Ｒ^１－Ｚ－（ＣＨ_２）_ｍ－である、項目１～３のいずれか一項に記載の化合物。
［６］
Ｒ^１１が、Ｒ^１－Ｚ－（ＣＨ_２）_ｍ－であり、ＺがＮＨである、項目１～３のいずれか一項に記載の化合物。
［７］
Ｒ^１１が、Ｒ^１－Ｚ－（ＣＨ_２）_ｍ－であり、ＺがＯである、項目１～３のいずれか一項に記載の化合物。
［８］
Ｒ^１１が、Ｒ^１－Ｚ－（ＣＨ_２）_ｍ－であり、ＺがＮＨであり、ｍが２である、項目１～３のいずれか一項に記載の化合物。
［９］
Ｒ^２がＨである、項目１～８のいずれか一項に記載の化合物。
［１０］
Ｒ^２がＣＨ_３である、項目１～８のいずれか一項に記載の化合物。
［１１］
Ｙが、－ＮＲ^４Ｒ^５Ｒ^６（＋）である、項目１～１０のいずれか一項に記載の化合物。
［１２］
Ｙが、－ＮＲ^４Ｒ^５Ｒ^６（＋）であり、Ｒ^４、Ｒ^５、およびＲ^６が独立して、ＣＨ_３である、項目１～１０のいずれか一項に記載の化合物。
［１３］
Ｙが、－ＮＲ^４Ｒ^５Ｒ^６（＋）であり、Ｒ^４およびＲ^５が独立して、ＣＨ^３であり、Ｒ^６が、Ｃ_２～Ｃ_１２芳香族アルキルである、項目１～１０のいずれか一項に記載の化合物。
［１４］
Ｙが、－ＮＲ^４Ｒ^５Ｒ^６（＋）であり、Ｒ^４およびＲ^５が独立して、ＣＨ_３であり、Ｒ^６が、－ＣＨ_２－Ｃ_６Ｈ_６である、項目１～１３のいずれか一項に記載の化合物。
［１５］
Ｙが、－ＮＲ^４Ｒ^５Ｒ^６（＋）であり、Ｙの対イオンが、塩化物、臭化物、フッ化物、ヨウ化物、酢酸塩、アルミン酸塩、シアン酸塩、シアン化物、ニ水素リン酸塩、亜リン酸二水素、ギ酸塩、炭酸塩、炭酸水素、シュウ酸水素、硫酸水素、水酸化物、硝酸塩、亜硝酸塩、チオシアン酸塩、またはそれらの組み合わせである、項目１～１４のいずれか一項に記載の化合物。
［１６］
Ｒ^３が、ＣＨ_２である、項目１～１５のいずれか一項に記載の化合物。
［１７］
Ｒ^３が、ＣＨ_２ＣＨ_２またはＣ（ＣＨ_３）_２である、項目１～１５のいずれか一項に記載の化合物。
［１８］
Ｒ^３が、非置換、直鎖、および飽和Ｃ_２～Ｃ_１０アルキレン基である、項目１～１５のいずれか一項に記載の化合物。
［１９］
Ｒ^３が、非置換、直鎖、および不飽和Ｃ_２～Ｃ_１０アルキレン基である、項目１～１５のいずれか一項に記載の化合物。
［２０］
Ｒ^１が、直鎖Ｃ_１～Ｃ_３０アルキル、アルケニル、またはアルキニル基である、項目１～１９のいずれか一項に記載の化合物。
［２１］
Ｒ^１が、分岐鎖Ｃ_３～Ｃ_３０アルキル、アルケニル、またはアルキニル基である、項目１～１９のいずれか一項に記載の化合物。
［２２］
Ｒ^１が、直鎖飽和Ｃ_１～Ｃ_３０アルキル基である、項目１～１９のいずれか一項に記載の化合物。
［２３］
Ｒ^１が、分岐鎖飽和Ｃ_１～Ｃ_３０アルキル基である、項目１～１９のいずれか一項に記載の化合物。
［２４］
Ｒ^１が、１つ以上の二重結合を有する直鎖Ｃ_１～Ｃ_３０アルケニル基である、項目１～１９のいずれか一項に記載の化合物。
［２５］
Ｒ^１が、１つ以上の二重結合を有する分岐鎖Ｃ_３～Ｃ_３０アルケニル基である、項目１～１９のいずれか一項に記載の化合物。
［２６］
Ｒ^１が、１つ以上の三重結合を有する直鎖Ｃ_２～Ｃ_３０アルキニル基である、項目１～１９のいずれか一項に記載の化合物。
［２７］
Ｒ^１が、１つ以上の三重結合を有する分岐鎖Ｃ_２～Ｃ_３０アルキニル基である、項目１～１９のいずれか一項に記載の化合物。
［２８］
Ｒ^１１が、直鎖および飽和Ｃ_２～Ｃ_２０アルキル基である、項目１～２７のいずれか一項に記載の化合物。
［２９］
Ｒ^１１が、少なくとも１つのトランス二重結合を有するＣ_２～Ｃ_２０アルケニル基である、項目１～２７のいずれか一項に記載の化合物。
［３０］
Ｒ^１１が、少なくとも１つのシス二重結合を有するＣ_２～Ｃ_２０アルケニル基である、項目１～２７のいずれか一項に記載の化合物。
［３１］
Ｒ^１１が、Ｒ^１Ｒ^１－ＮＨ－ＣＨ_２ＣＨ_２ＣＨ_２基であり、Ｒ^１が、飽和直鎖Ｃ_２～Ｃ_２０アルキル、トランスアルケニル、またはシスアルケニル基である、項目１～２７のいずれか一項に記載の化合物。
［３２］
Ｒ^２が、Ｈであり、Ｘが、ＮＨであり、Ｒ^３が、ＣＨ_２ＣＨ_２であり、Ｙが、ＣＨ_２－Ｎ^＋（ＣＨ_３）_３Ｃｌ^－である、項目１～３１のいずれか一項に記載の化合物。
［３３］
化合物を合成するための方法であって、
一級アミンを活性化オレフィンと接触させて、項目１～３２のいずれか一項に記載の化合物を生成することを含み、
前記一級アミンが、Ｒ^１１－ＮＨ_２であり、Ｒ^１１が、Ｒ^１またはＲ^１－Ｚ－（ＣＨ_２）_ｍ－であり、
前記活性化オレフィンが、

であり、Ｘが、ＮＨまたはＯであり、
Ｒ^１１が、Ｒ^１またはＲ^１－Ｚ－（ＣＨ_２）_ｍ－であり、
Ｒ^１が、非置換もしくは置換の直鎖もしくは分岐鎖Ｃ_１～Ｃ_３０アルキル、環状アルキル、アルケニル、またはアルキニル基であり、
Ｚが、ＮＨまたはＯであり、
Ｒ^２が、Ｈ、ＣＨ_３、または非置換の直鎖もしくは分岐鎖Ｃ_２～Ｃ_１０アルキル、アルケニル、もしくはアルキニル基であり、
ｍが、１～４の整数であり、
Ｒ^３が、存在しないか、または非置換の直鎖Ｃ_{１～Ｃ３０}アルキレン基であり、
Ｙが、－ＮＲ^４Ｒ^５Ｒ^６（＋）、またはその塩であり、
Ｒ^４、Ｒ^５、およびＲ^６が独立して、Ｃ_１～Ｃ_１０アルキル基である、方法。
［３４］
前記接触ステップが、反応溶媒、反応溶媒およびアルカリ源、反応溶媒および酸、または反応溶媒および触媒の存在下で行われる、項目３３に記載の方法。
［３５］
前記反応溶媒が、水、メタノール、エタノール、プロパノール、グリコール、ＰＥＧ、またはそれらの混合物である、項目３４に記載の方法。
［３６］
前記反応溶媒が、水である、項目３４に記載の方法。
［３７］
前記接触ステップが、触媒、塩基、またはそれらの組み合わせの存在下で行われる、項目３３～３６のいずれか一項に記載の方法。
［３８］
前記接触ステップが、触媒、塩基、または酸の存在なしで行われる、項目３３～３６のいずれか一項に記載の方法。
［３９］
前記接触ステップが、塩基の存在下で行われる、項目３３～３６のいずれか一項に記載の方法。
［４０］
前記接触ステップが、塩基、酸、または触媒なしで行われる、項目３３～３６のいずれか一項に記載の方法。
［４１］
前記接触ステップが、水酸化物、アルカリ金属水酸化物（ａｌｋａｌｉ ｍｅｔａｌ ｈｙｄｒｏｘｉｄｅ）、アルカリ金属水酸化物（ａｌｋａｌｉｎｅ ｍｅｔａｌ ｈｙｄｒｏｘｉｄｅ）、金属炭酸塩、イミダゾール、ピリジン系塩基、アミジン塩基、グアニジン塩基、またはそれらの組み合わせの存在下で行われる、項目３３～３７のいずれか一項に記載の方法。
［４２］
前記接触ステップが、ベンジルトリメチルアンモニウムヒドロキシドの存在下で行われる、項目３３～３６のいずれか一項に記載の方法。
［４３］
項目１～３２のいずれか一項に記載の１つ以上の化合物を含む物品、製品、または組成物。
［４４］
前記物品、製品、または組成物が、担体溶媒をさらに含む、項目４３に記載の物品、製品、または組成物。
［４５］
前記物品、製品、または組成物が、水をさらに含む、項目４３又は４４に記載の物品、製品、または組成物。
［４６］
前記担体溶媒が、水、アルコール、アルキレングリコール、アルキレングリコールアルキルエーテル、またはそれらの組み合わせである、項目４３又は４４に記載の物品、製品、または組成物。
［４７］
前記担体溶媒が、メタノール、エタノール、プロパノール、イソプロパノール、ブタノール、イソブタノール、モノエチレングリコール、エチレングリコールモノブチルエーテル、またはそれらの組み合わせである、項目４３～４５のいずれか一項に記載の物品、製品、または組成物。
［４８］
前記物品、製品、または組成物が、一次アルカリ源をさらに含み、洗剤組成物である、項目４３～４７のいずれか一項に記載の物品、製品、または組成物。
［４９］
前記一次アルカリ源が、アルカリ金属水酸化物、アルカリ金属炭酸塩、アルカリ金属ケイ酸塩、アルカリ金属メタケイ酸塩、アルカノアミン、アミン、またはそれらの混合物である、項目４８に記載の物品、製品、または組成物。
［５０］
前記一次アルカリ源が、アルカリ金属水酸化物、アルカリ金属炭酸塩、またはそれらの混合物である、項目４８に記載の物品、製品、または組成物。
［５１］
前記一次アルカリ源が、アルカリ金属炭酸塩である、項目４８に記載の物品、製品、または組成物。
［５２］
前記物品、製品、または組成物が、ビルダーをさらに含む、項目４８～５１のいずれか一項に記載の物品、製品、または組成物。
［５３］
前記物品、製品、または組成物が、酵素をさらに含む、項目４８～５２のいずれか一項に記載の物品、製品、または組成物。
［５４］
前記酵素が、プロテアーゼ酵素である、項目５３に記載の物品、製品、または組成物。
［５５］
前記物品、製品、または組成物が、キレート剤をさらに含む、項目４８～５４のいずれか一項に記載の物品、製品、または組成物。
［５６］
前記キレート剤が、メチルグリシン二酢酸（ＭＧＤＡ）、グルタミン酸－Ｎ，Ｎ－二酢酸（ＧＬＤＡ）、Ｎ－ヒドロキシエチルアミノ二酢酸、エチレンジアミン四酢酸（ＥＤＴＡ）、ヒドロキシエチレンジアミン四酢酸、ジエチレントリアミン五酢酸、Ｎ－ヒドロキシエチル－エチレンジアミン三酢酸（ＨＥＤＴＡ）、ジエチレントリアミン五酢酸（ＤＴＰＡ）、エチレンジアミンコハク酸（ＥＤＤＳ）、２－ヒドロキシエチルイミノ二酢酸（ＨＥＩＤＡ）、イミノジコハク酸（ＩＤＳ）、３－ヒドロキシ－２－２’－イミノジコハク酸（ＨＩＤＳ）、またはそれらの混合物である、項目５５に記載の物品、製品、または組成物。
［５７］
前記物品、製品、または組成物が、１つ以上の追加の洗剤組成物剤をさらに含む、項目４８～５６のいずれか一項に記載の物品、製品、または組成物。
［５８］
前記物品、製品、または組成物が、界面活性剤をさらに含む、項目４３～５７のいずれか一項に記載の物品、製品、または組成物。
［５９］
前記界面活性剤が、非イオン性、半非イオン性、カチオン性、アニオン性、両性、双性イオン性、ジェミニ界面活性剤、またはそれらの混合物である、項目５８に記載の物品、製品、または組成物。
［６０］
前記組成物が、固体、多重使用固体、または多重使用プレス固体組成物である、項目４８～５９のいずれか一項に記載の物品、製品、または組成物。
［６１］
水系中の表面における腐食を抑制するための方法であって、
腐食制御組成物または前記腐食制御組成物の使用溶液を水系中に提供して、処理された水系を生成することか、または前記水系の表面上に提供することを含み、
前記腐食制御組成物が、式Ｉ、式ＩＩ、式ＩＩＩのうちの１つによる１つ以上の化合物と、１つ以上の追加の腐食制御組成物剤とを含み、

式中、
Ｘが、ＮＨまたはＯであり、
Ｒ^１１が、Ｒ^１またはＲ^１－Ｚ－（ＣＨ_２）_ｍ－であり、
Ｒ^１が、非置換もしくは置換の直鎖もしくは分岐鎖Ｃ_５～Ｃ_３０アルキル、環状アルキル、アルケニル、またはアルキニル基であり、
Ｚが、ＮＨまたはＯであり、
Ｒ^２が、Ｈ、ＣＨ_３、または非置換の直鎖もしくは分岐鎖Ｃ_２～Ｃ_１０アルキル、アルケニル、もしくはアルキニル基であり、
ｍが、１～４の整数であり、
Ｒ^３が、存在しないか、または非置換の直鎖Ｃ_１～Ｃ_３０アルキレン基であり、
Ｙが、－ＮＲ^４Ｒ^５Ｒ^６（＋）であり、
Ｙ’が、－ＣＯＯＨ、－ＳＯ_３Ｈ、－ＰＯ_３Ｈ、－ＯＳＯ_３Ｈ、－ＯＰＯ_３Ｈ、またはそれらの塩であり、
Ｒ^４、Ｒ^５、およびＲ^６が独立して、Ｃ_１～Ｃ_１０アルキル基であり、
Ｒ^２’が、Ｈ、ＣＨ_３、または非置換もしくは置換の直鎖もしくは分岐鎖Ｃ_１～Ｃ_１０アルキル、アルケニル、アルキニル基、－ＣＯＯＨ、－ＣＨ_２ＣＯＯＨ、Ｙ’、または－（ＣＨ_２）_ｍ－Ｙ’であり、
前記腐食制御組成物が、前記水系中の前記表面上の腐食を緩和する、方法。
［６２］
ＸがＮＨである、項目６１に記載の方法。
［６３］
ＸがＯである、項目６１に記載の方法。
［６４］
Ｒ^１１が、Ｒ^１であり、Ｒ^１が、直鎖Ｃ_５～Ｃ_３０アルキル、アルケニル、またはアルキニル基である、項目６１～６３のいずれか一項に記載の方法。
［６５］
Ｒ^１１が、Ｒ^１－Ｚ－（ＣＨ_２）_ｍ－またはＲ^１－Ｚ－（ＣＨ_２）_２－であり、Ｚが、ＮＨであり、Ｒ^１が、直鎖Ｃ_５～Ｃ_３０アルキル、アルケニル、またはアルキニル基である、項目６１～６３のいずれか一項に記載の方法。
［６６］
Ｒ^１１が、Ｒ^１－Ｚ－（ＣＨ_２）_ｍ－であり、Ｚが、Ｏであり、Ｒ^１が、直鎖Ｃ_５～Ｃ_３０アルキル、アルケニル、またはアルキニル基である、項目６１～６３のいずれか一項に記載の方法。
［６７］
Ｒ^２が、ＨまたはＣＨ_３である、項目６１～６６のいずれか一項に記載の方法。
［６８］
Ｙが、－ＮＲ^４Ｒ^５Ｒ^６（＋）、Ｎ（ＣＨ_３）_３ ^＋、Ｎ（ＣＨ_３）_２Ｒ_６ ^＋であり、Ｒ^６が、Ｃ_２～Ｃ_１２アルキル、アリール、または－ＣＨ_２～Ｃ_６Ｈ_６である、項目６１～６７のいずれか一項に記載の方法。
［６９］
Ｒ^３が、ＣＨ_２、ＣＨ_２ＣＨ_２、またはＣ（ＣＨ_３）_２、非置換および直鎖Ｃ_２～Ｃ_１０アルキレン基である、項目６１～６８のいずれか一項に記載の方法。
［７０］
Ｒ^１１が、少なくとも１つのトランスまたはシス二重結合を有するＣ_６～Ｃ_２０アルケニル基である、項目６１～６９のいずれか一項に記載の方法。
［７１］
前記腐食制御組成物剤が、担体であり、前記担体が、水、有機溶媒、またはそれらの混合物である、項目６１～７０のいずれか一項に記載の方法。
［７２］
前記腐食制御組成物剤が、担体および１つ以上の追加の腐食抑制剤である、項目６１～７１のいずれか一項に記載の方法。
［７３］
前記腐食制御組成物剤が、殺生物剤であり、前記殺生物剤が、塩素、次亜塩素酸塩、ＣｌＯ_２、臭化物、オゾン、過酸化水素、過酢酸、ペルオキシ硫酸、ペルオキシカルボン酸組成物、グルタルアルデヒド、ジブロモニトリロプロピオンアミド、イソチアゾロン、テルブチラジン、高分子ビグアニド、メチレンビスチオシアネート、テトラキスヒドロキシメチルホスホニウムサルフェート、またはそれらの任意の組み合わせである、項目６１～７２のいずれか一項に記載の方法。
［７４］
前記腐食制御組成物剤が、酸であり、前記腐食制御組成物が、約１重量％～約２０重量％の前記酸を含み、前記酸が、塩酸、フッ化水素酸、クエン酸、ギ酸、酢酸、またはそれらの混合物である、項目６１～７３のいずれか一項に記載の方法。
［７５］
前記腐食制御組成物剤が、界面活性剤である、項目６１～７４のいずれか一項に記載の方法。
［７６］
前記腐食制御組成物剤が、スケール抑制剤、ガスハイドレート抑制剤、ｐＨ調整剤、またはそれらの任意の組み合わせである、項目６１～７５のいずれか一項に記載の方法。
［７７］
前記腐食制御組成物剤が、エマルジョン破壊剤、逆エマルジョン破壊剤、汚損制御剤、凝固剤／凝集剤、乳化剤（ｅｍｕｌｓｉｆｉｅｒ）、水浄化剤、分散剤、酸化防止剤、ポリマー分解防止剤、浸透性調整剤、発泡剤、消泡剤、乳化剤（ｅｍｕｌｓｉｆｙｉｎｇ ａｇｅｎｔ）、ＣＯ_２および／またはＯ_２の捕捉剤、ゲル化剤、潤滑剤、摩擦低減剤、塩、またはそれらの混合物である、項目６１～７６のいずれか一項に記載の方法。
［７８］
前記腐食制御組成物が、液体、ゲル、または液体／ゲルおよび固体を含む混合物である、項目６１～７７のいずれか一項に記載の方法。
［７９］
前記腐食制御組成物またはその使用溶液が、約１～約１１のｐＨを有する、項目６１～７８のいずれか一項に記載の方法。
［８０］
前記腐食制御組成物が、前記組成物の約１０重量％～約８０重量％を構成する、項目６１～７９のいずれか一項に記載の方法。
［８１］
前記化合物が、前記処理された水系中で約１ｐｐｍ～約１０００ｐｐｍの濃度を有する、項目６１～８０のいずれか一項に記載の方法。
［８２］
前記水系が、淡水、プロセス水、塩水、地表水、随伴水、油、炭化水素、固体、またはそれらの混合物を含む、項目６１～８１のいずれか一項に記載の方法。
［８３］
前記水系が、冷却水系、ボイラー水系、石油およびガス操業における水系、石油坑、ダウンホール形成、地熱井、鉱物洗浄、浮選および慈善、製紙、ガススクラバ、エアウォッシャ、冶金工業の連続鋳造プロセス、空調および冷蔵、水の再生利用、浄水、膜濾過、食品加工、浄化器、都市下水処理、都市水処理、または飲料水系である、項目６１～８２のいずれか一項に記載の方法。
［８４］
式Ｉ、式ＩＩ、式ＩＩＩのうちの１つによる１つ以上の化合物と、１つ以上の追加の腐食制御組成物剤とを含む、腐食制御組成物であって、

式中、
Ｘが、ＮＨまたはＯであり、
Ｒ^１１が、Ｒ^１またはＲ^１－Ｚ－（ＣＨ_２）_ｍ－であり、
Ｒ^１が、非置換もしくは置換の直鎖もしくは分岐鎖Ｃ_５～Ｃ_３０アルキル、環状アルキル、アルケニル、またはアルキニル基であり、
Ｚが、ＮＨまたはＯであり、
Ｒ^２が、Ｈ、ＣＨ_３、または非置換の直鎖もしくは分岐鎖Ｃ_２～Ｃ_１０アルキル、アルケニル、もしくはアルキニル基であり、
ｍが、１～４の整数であり、
Ｒ^３が、存在しないか、または非置換の直鎖Ｃ_{１～Ｃ３０}アルキレン基であり、
Ｙが、－ＮＲ^４Ｒ^５Ｒ^６（＋）であり、
Ｙ’が、－ＣＯＯＨ、－ＳＯ_３Ｈ、－ＰＯ_３Ｈ、－ＯＳＯ_３Ｈ、－ＯＰＯ_３Ｈ、またはそれらの塩であり、
Ｒ^４、Ｒ^５、およびＲ^６が独立して、Ｃ_１～Ｃ_１０アルキル基であり、
Ｒ^２’が、Ｈ、ＣＨ_３、または非置換もしくは置換の直鎖もしくは分岐鎖Ｃ_１～Ｃ_１０アルキル、アルケニル、アルキニル基、－ＣＯＯＨ、－ＣＨ_２ＣＯＯＨ、Ｙ’、または－（ＣＨ_２）_ｍ－Ｙ’であり、
前記腐食制御組成物が、前記水系中の前記表面の腐食を緩和する、腐食制御組成物。 The above specification provides a description of the novel compounds, their synthesis and uses, as well as compositions, articles of manufacture, or articles comprising the disclosed compounds. Since many embodiments can be made without departing from the spirit and scope of the disclosure, the invention resides in the claims. Examples of embodiments of the present invention are listed below.
[1]
A compound according to Formula I,

During the ceremony,
X is NH or O;
R ¹¹ is R ¹ or R ¹ -Z-(CH ₂ ) _m -,
R ¹ is an unsubstituted or substituted straight or branched chain C ₁ -C ₃₀ alkyl, cyclic alkyl, alkenyl, or alkynyl group;
Z is NH or O;
R ² is H, CH ₃ , or an unsubstituted straight or branched chain C ₂ -C ₁₀ alkyl, alkenyl, or alkynyl group;
m is an integer from 1 to 4,
R ³ is absent or an unsubstituted linear C1 _-C30 alkylene group;
Y is —NR ⁴ R ⁵ R ⁶⁽⁺⁾ , or a salt thereof;
A compound wherein R ⁴ , R ⁵ , and R ⁶ are independently C ₁ -C ₁₀ alkyl groups.
[2]
The compound according to item 1, wherein X is NH.
[3]
The compound according to item 1, wherein X is O.
[4]
A compound according to any one of items 1-3, wherein R ¹¹ is R ¹ .
[5]
The compound according to any one of items 1-3, wherein R ¹¹ is R ¹ -Z-(CH ₂ ) _m -.
[6]
The compound according to any one of items 1-3, wherein R ¹¹ is R ¹ -Z-(CH ₂ ) _m - and Z is NH.
[7]
The compound according to any one of items 1-3, wherein R ¹¹ is R ¹ -Z-(CH ₂ ) _m -, and Z is O.
[8]
The compound according to any one of items 1-3, wherein R ¹¹ is R ¹ -Z-(CH ₂ ) _m -, Z is NH and m is 2.
[9]
The compound according to any one of items 1-8, wherein R ² is H.
[10]
The compound according to any one of items 1-8, wherein R ² is CH ₃ .
[11]
The compound according to any one of items 1 to 10, wherein Y is -NR ⁴ R ⁵ R ⁶⁽⁺⁾ .
[12]
The compound according to any one of items 1 to 10, wherein Y is -NR ⁴ R ⁵ R ⁶⁽⁺⁾ and R ⁴ , R ⁵ and R ⁶ are independently CH ₃ .
[13]
Items 1-10 wherein Y is -NR ⁴ R ⁵ R ⁶⁽⁺⁾ , R ⁴ and R ⁵ are independently CH ³ and R ⁶ is C ₂ -C ₁₂ aromatic alkyl A compound according to any one of
[14]
Items 1-13 wherein Y is -NR ⁴ R ⁵ R ⁶⁽⁺⁾ , R ⁴ and R ⁵ are independently CH ₃ and R ⁶ is -CH ₂ -C ₆ H ₆ A compound according to any one of
[15]
Y is -NR ⁴ R ⁵ R ^{6 (+)} and the counterion of Y is chloride, bromide, fluoride, iodide, acetate, aluminate, cyanate, cyanide, dihydrogen phosphorus acid, dihydrogen phosphite, formate, carbonate, hydrogen carbonate, hydrogen oxalate, hydrogen sulfate, hydroxide, nitrate, nitrite, thiocyanate, or combinations thereof, of items 1 to 14 A compound according to any one of clauses.
[16]
The compound according to any one of items 1-15, wherein R ³ is CH ₂ .
[17]
Compounds according to any one of items 1-15, wherein R ³ is CH ₂ CH ₂ or C(CH ₃ ) ₂ .
[18]
Compounds according to any one of items 1-15, wherein R ³ is an unsubstituted, straight chain and saturated C ₂ -C ₁₀ alkylene group.
[19]
A compound according to any one of items 1 to 15, wherein R ³ is an unsubstituted, linear and unsaturated C ₂ -C ₁₀ alkylene group.
[20]
20. The compound according to any one of items 1-19, wherein R ¹ is a straight chain C ₁ -C ₃₀ alkyl, alkenyl, or alkynyl group.
[21]
The compound according to any one of items 1-19, wherein R ¹ is a branched C ₃ -C ₃₀ alkyl, alkenyl, or alkynyl group.
[22]
20. The compound according to any one of items 1-19, wherein R ¹ is a linear saturated C ₁ -C ₃₀ alkyl group.
[23]
Compounds according to any one of items 1-19, wherein R ¹ is a branched saturated C ₁ -C ₃₀ alkyl group.
[24]
Compounds according to any one of items 1-19, wherein R ¹ is a straight chain C ₁ -C ₃₀ alkenyl group having one or more double bonds.
[25]
A compound according to any one of items 1-19, wherein R ¹ is a branched C ₃ -C ₃₀ alkenyl group having one or more double bonds.
[26]
A compound according to any one of items 1-19, wherein R ¹ is a straight chain C ₂ -C ₃₀ alkynyl group having one or more triple bonds.
[27]
A compound according to any one of items 1-19, wherein R ¹ is a branched C ₂ -C ₃₀ alkynyl group having one or more triple bonds.
[28]
Compounds according to any one of items 1-27, wherein R ¹¹ is a linear and saturated C ₂ -C ₂₀ alkyl group.
[29]
Compounds according to any one of items 1-27, wherein R ¹¹ is a C ₂ -C ₂₀ alkenyl group having at least one trans double bond.
[30]
Compounds according to any one of items 1-27, wherein R ¹¹ is a C ₂ -C ₂₀ alkenyl group having at least one cis double bond.
[31]
^{The _ _} _{_ _ _} ^_ _{_ _} A compound according to any one of clauses.
[32]
any of items 1 to 31, wherein R ² is H, X is NH, R ³ is CH ₂ CH ₂ and Y is CH ₂ —N ⁺ (CH ₃ ) ₃ Cl ^— or the compound according to item 1.
[33]
A method for synthesizing a compound comprising:
contacting a primary amine with an activated olefin to produce a compound according to any one of items 1-32;
the primary amine is R ¹¹ —NH ₂ , R ¹¹ is R ¹ or R ¹ —Z—(CH ₂ ) _m —;
The activated olefin is

and X is NH or O;
R ¹¹ is R ¹ or R ¹ -Z-(CH ₂ ) _m -,
R ¹ is an unsubstituted or substituted straight or branched chain C ₁ -C ₃₀ alkyl, cyclic alkyl, alkenyl, or alkynyl group;
Z is NH or O;
R ² is H, CH ₃ , or an unsubstituted straight or branched chain C ₂ -C ₁₀ alkyl, alkenyl, or alkynyl group;
m is an integer from 1 to 4,
R ³ is absent or an unsubstituted linear C1 _-C30 alkylene group;
Y is —NR ⁴ R ⁵ R ⁶⁽⁺⁾ , or a salt thereof;
The method wherein R ⁴ , R ⁵ and R ⁶ are independently C ₁ -C ₁₀ alkyl groups.
[34]
34. The method of item 33, wherein the contacting step is performed in the presence of a reaction solvent, a reaction solvent and an alkalinity source, a reaction solvent and an acid, or a reaction solvent and a catalyst.
[35]
35. The method of item 34, wherein the reaction solvent is water, methanol, ethanol, propanol, glycol, PEG, or mixtures thereof.
[36]
35. The method of item 34, wherein the reaction solvent is water.
[37]
37. The method of any one of items 33-36, wherein said contacting step is performed in the presence of a catalyst, a base, or a combination thereof.
[38]
37. The method of any one of items 33-36, wherein said contacting step is performed without the presence of a catalyst, base, or acid.
[39]
37. The method of any one of items 33-36, wherein said contacting step is performed in the presence of a base.
[40]
37. The method of any one of items 33-36, wherein said contacting step is performed without a base, acid, or catalyst.
[41]
The contacting step is a hydroxide, an alkali metal hydroxide, an alkali metal hydroxide, a metal carbonate, an imidazole, a pyridine base, an amidine base, a guanidine base, or 38. A method according to any one of items 33-37, carried out in the presence of a combination.
[42]
37. The method of any one of items 33-36, wherein said contacting step is performed in the presence of benzyltrimethylammonium hydroxide.
[43]
An article, product, or composition comprising one or more compounds according to any one of items 1-32.
[44]
44. The article, product, or composition of item 43, wherein said article, product, or composition further comprises a carrier solvent.
[45]
45. The article, product or composition of items 43 or 44, wherein said article, product or composition further comprises water.
[46]
45. The article, product, or composition of items 43 or 44, wherein the carrier solvent is water, alcohol, alkylene glycol, alkylene glycol alkyl ether, or combinations thereof.
[47]
46. The article, product of any one of items 43-45, wherein the carrier solvent is methanol, ethanol, propanol, isopropanol, butanol, isobutanol, monoethylene glycol, ethylene glycol monobutyl ether, or combinations thereof, Or composition.
[48]
48. The article, product or composition of any one of items 43-47, wherein said article, product or composition further comprises a primary alkalinity source and is a detergent composition.
[49]
49. The article, product of item 48, wherein said primary alkalinity source is an alkali metal hydroxide, alkali metal carbonate, alkali metal silicate, alkali metal metasilicate, alkanoamine, amine, or mixtures thereof. Or composition.
[50]
49. The article, product, or composition of item 48, wherein the primary alkalinity source is an alkali metal hydroxide, an alkali metal carbonate, or a mixture thereof.
[51]
49. The article, product, or composition of item 48, wherein the primary alkalinity source is an alkali metal carbonate.
[52]
52. The article, product or composition of any one of items 48-51, wherein said article, product or composition further comprises a builder.
[53]
53. The article, product or composition of any one of items 48-52, wherein said article, product or composition further comprises an enzyme.
[54]
54. The article, product, or composition of item 53, wherein said enzyme is a protease enzyme.
[55]
55. The article, product or composition of any one of items 48-54, wherein said article, product or composition further comprises a chelating agent.
[56]
The chelating agent is methylglycinediacetic acid (MGDA), glutamic acid-N,N-diacetic acid (GLDA), N-hydroxyethylaminodiacetic acid, ethylenediaminetetraacetic acid (EDTA), hydroxyethylenediaminetetraacetic acid, diethylenetriaminepentaacetic acid, N -hydroxyethyl-ethylenediaminetriacetic acid (HEDTA), diethylenetriaminepentaacetic acid (DTPA), ethylenediaminesuccinic acid (EDDS), 2-hydroxyethyliminodiacetic acid (HEIDA), iminodisuccinic acid (IDS), 3-hydroxy-2-2' - The article, product or composition according to item 55, which is iminodisuccinic acid (HIDS), or mixtures thereof.
[57]
57. The article, product or composition of any one of items 48-56, wherein said article, product or composition further comprises one or more additional detergent composition agents.
[58]
58. The article, product or composition of any one of items 43-57, wherein said article, product or composition further comprises a surfactant.
[59]
59. The article, manufacture, or of item 58, wherein said surfactant is a nonionic, semi-nonionic, cationic, anionic, amphoteric, zwitterionic, gemini surfactant, or mixtures thereof. Composition.
[60]
60. The article, product, or composition of any one of items 48-59, wherein said composition is a solid, a multi-use solid, or a multi-use pressed solid composition.
[61]
A method for inhibiting corrosion on a surface in an aqueous system comprising:
providing a corrosion control composition or a use solution of said corrosion control composition into a water system to produce a treated water system or on a surface of said water system;
wherein the corrosion control composition comprises one or more compounds according to one of Formula I, Formula II, Formula III and one or more additional corrosion control composition agents;

During the ceremony,
X is NH or O;
R ¹¹ is R ¹ or R ¹ -Z-(CH ₂ ) _m -,
R ¹ is an unsubstituted or substituted straight or branched chain C ₅ -C ₃₀ alkyl, cyclic alkyl, alkenyl, or alkynyl group;
Z is NH or O;
R ² is H, CH ₃ , or an unsubstituted straight or branched chain C ₂ -C ₁₀ alkyl, alkenyl, or alkynyl group;
m is an integer from 1 to 4,
R ³ is absent or an unsubstituted linear C ₁ -C ₃₀ alkylene group;
Y is -NR ⁴ R ⁵ R ^{6 (+)} ;
Y′ is —COOH, —SO ₃ H, —PO ₃ H, —OSO ₃ H, —OPO ₃ H, or a salt thereof;
R ⁴ , R ⁵ , and R ⁶ are independently C ₁ -C ₁₀ alkyl groups;
R ² ' is H, CH ₃ , or an unsubstituted or substituted straight or branched chain C ₁ -C ₁₀ alkyl, alkenyl, alkynyl group, —COOH, —CH ₂ COOH, Y', or —(CH ₂ ) _m -Y',
The method, wherein the corrosion control composition mitigates corrosion on the surface in the aqueous system.
[62]
62. The method of item 61, wherein X is NH.
[63]
62. The method of item 61, wherein X is O.
[64]
64. The method of any one of items 61-63, wherein R ¹¹ is R ¹ and R ¹ is a linear C ₅ -C ₃₀ alkyl, alkenyl, or alkynyl group.
[65]
R ¹¹ is R ¹ -Z-(CH ₂ ) _m - or R ¹ -Z-(CH ₂ ) ₂ -, Z is NH, R ¹ is linear C ₅ -C ₃₀ alkyl, A method according to any one of items 61 to 63, which is an alkenyl or alkynyl group.
[66]
Items 61-63 wherein R ¹¹ is R ¹ -Z-(CH ₂ ) _m -, Z is O, and R ¹ is a linear C ₅ -C ₃₀ alkyl, alkenyl, or alkynyl group The method according to any one of .
[67]
67. The method of any one of items 61-66, wherein R ² is H or CH ₃ .
[68]
Y is -NR ⁴ R ⁵ R ⁶⁽⁺⁾ , N(CH ₃ ) ₃ ⁺ , N(CH ₃ ) ₂ R ₆ ⁺ and R ⁶ is C ₂ -C ₁₂ alkyl, aryl, or -CH 68. The method of any one of items 61-67, wherein the compound is ₂ -C ₆ H ₆ .
[69]
69. The method of any one of items 61-68, wherein R ³ is CH ₂ , CH ₂ CH ₂ , or C(CH ₃ ) ₂ , an unsubstituted and linear C ₂ -C ₁₀ alkylene group.
[70]
The method according to any one of items 61-69, wherein R ¹¹ is a C ₆ -C ₂₀ alkenyl group having at least one trans or cis double bond.
[71]
71. The method of any one of items 61-70, wherein the corrosion control composition agent is a carrier, and the carrier is water, an organic solvent, or a mixture thereof.
[72]
72. The method of any one of items 61-71, wherein the corrosion control composition agent is a carrier and one or more additional corrosion inhibitors.
[73]
The corrosion control composition agent is a biocide, and the biocide is chlorine, hypochlorite, _ClO2 , bromide, ozone, hydrogen peroxide, peracetic acid, peroxysulfuric acid, peroxycarboxylic acid composition. , glutaraldehyde, dibromonitrilopropionamide, isothiazolone, terbuthylazine, polymeric biguanide, methylenebisthiocyanate, tetrakishydroxymethylphosphonium sulfate, or any combination thereof.
[74]
wherein said corrosion control composition agent is an acid, said corrosion control composition comprises from about 1% to about 20% by weight of said acid, said acid being hydrochloric acid, hydrofluoric acid, citric acid, formic acid, 74. The method of any one of items 61-73, which is acetic acid, or a mixture thereof.
[75]
75. The method of any one of items 61-74, wherein the corrosion control composition agent is a surfactant.
[76]
76. The method of any one of items 61-75, wherein the corrosion control composition agent is a scale inhibitor, a gas hydrate inhibitor, a pH adjuster, or any combination thereof.
[77]
The corrosion control composition includes emulsion breakers, inverse emulsion breakers, fouling control agents, coagulants/flocculants, emulsifiers, water purification agents, dispersants, antioxidants, polymeric antidegradants, penetrating agents, Items 61- which are modifiers, blowing agents, defoamers, emulsifying agents, _CO2 and/or _O2 scavengers, gelling agents, lubricants, friction reducers, salts, or mixtures thereof 76. The method of any one of clauses 76.
[78]
78. The method of any one of items 61-77, wherein the corrosion control composition is a liquid, a gel, or a mixture comprising a liquid/gel and a solid.
[79]
79. The method of any one of items 61-78, wherein the corrosion control composition or use solution thereof has a pH of about 1 to about 11.
[80]
80. The method of any one of items 61-79, wherein the corrosion control composition comprises from about 10% to about 80% by weight of the composition.
[81]
81. The method of any one of items 61-80, wherein said compound has a concentration in said treated aqueous system of from about 1 ppm to about 1000 ppm.
[82]
82. The method of any one of items 61-81, wherein the aqueous system comprises fresh water, process water, salt water, surface water, produced water, oil, hydrocarbons, solids, or mixtures thereof.
[83]
Said water systems include cooling water systems, boiler water systems, water systems in oil and gas operations, oil wells, downhole formation, geothermal wells, mineral washing, flotation and charities, papermaking, gas scrubbers, air washers, continuous casting processes in the metallurgical industry, air conditioning. and refrigeration, water recycling, water purification, membrane filtration, food processing, clarifiers, municipal sewage treatment, municipal water treatment, or drinking water systems.
[84]
A corrosion control composition comprising one or more compounds according to one of Formula I, Formula II, Formula III and one or more additional corrosion control composition agents,

During the ceremony,
X is NH or O;
R ¹¹ is R ¹ or R ¹ -Z-(CH ₂ ) _m -,
R ¹ is an unsubstituted or substituted straight or branched chain C ₅ -C ₃₀ alkyl, cyclic alkyl, alkenyl, or alkynyl group;
Z is NH or O;
R ² is H, CH ₃ , or an unsubstituted straight or branched chain C ₂ -C ₁₀ alkyl, alkenyl, or alkynyl group;
m is an integer from 1 to 4,
R ³ is absent or an unsubstituted linear C1 _-C30 alkylene group;
Y is -NR ⁴ R ⁵ R ^{6 (+)} ;
Y′ is —COOH, —SO ₃ H, —PO ₃ H, —OSO ₃ H, —OPO ₃ H, or a salt thereof;
R ⁴ , R ⁵ , and R ⁶ are independently C ₁ -C ₁₀ alkyl groups;
R ² ' is H, CH ₃ , or an unsubstituted or substituted straight or branched chain C ₁ -C ₁₀ alkyl, alkenyl, alkynyl group, —COOH, —CH ₂ COOH, Y', or —(CH ₂ ) _m -Y',
A corrosion control composition, wherein said corrosion control composition mitigates corrosion of said surface in said aqueous system.

Claims (25)

A compound according to Formula I,

During the ceremony,
X is NH;
R ¹¹ is a C ₆ -C ₂₀ alkenyl group having at least one trans or cis double bond;
^R2 is H or _CH3 ;
R ³ is CH ₂ , CH ₂ CH ₂ , or C(CH ₃ ) ₂ ;
Y is —NR ⁴ R ⁵ R ⁶⁽⁺⁾ , or a salt thereof;
A compound wherein R ⁴ and R ⁵ are independently CH ₃ and R ⁶ is CH ₃ , C ₂ -C ₁₂ aromatic alkyl, or —CH ₂ —C ₆ H ₅ . Y is -NR ⁴ R ⁵ R ^{6 (+)} and the counterion of Y is chloride, bromide, fluoride, iodide, acetate, aluminate, cyanate, cyanide, dihydrogen phosphorus acid, dihydrogen phosphite, formate, carbonate, hydrogen carbonate, hydrogen oxalate, hydrogen sulfate, hydroxide, nitrate, nitrite, thiocyanate, or combinations thereof. compound. A compound according to claim 1 or 2, wherein R ² is H and Y is -N ⁺ (CH ₃ ) ₃ Cl ^- . A method for synthesizing a compound comprising:
contacting a primary amine with an activated olefin to produce a compound according to any one of claims 1-3;
the primary amine is R ¹¹ —NH ₂ ;
The activated olefin is

and X is NH;
R ¹¹ is a C ₆ -C ₂₀ alkenyl group having at least one trans or cis double bond;
^R2 is H or _CH3 ;
R ³ is CH ₂ , CH ₂ CH ₂ , or C(CH ₃ ) ₂ ;
Y is —NR ⁴ R ⁵ R ⁶⁽⁺⁾ , or a salt thereof;
The method wherein R ⁴ and R ⁵ are independently CH ₃ and R ⁶ is CH ₃ , C ₂ -C ₁₂ aromatic alkyl, or —CH ₂ —C ₆ H ₅ . The contacting step is performed in the presence of a reaction solvent, a reaction solvent and an alkalinity source, a reaction solvent and an acid, or a reaction solvent and a catalyst, wherein the reaction solvent is water, methanol, ethanol, propanol, glycol, PEG, or 5. The method of claim 4, which is a mixture of 5. The method of claim 4, wherein said contacting step is performed in the presence of a catalyst, a base, or a combination thereof. 5. The method of claim 4, wherein said contacting step is performed without the presence of a catalyst, base, or acid. The contacting step is a hydroxide, an alkali metal hydroxide, an alkali metal hydroxide, a metal carbonate, an imidazole, a pyridine base, an amidine base, a guanidine base, or 7. A method according to claim 5 or 6, carried out in the presence of a combination. 7. The method of claim 5 or 6, wherein said contacting step is performed in the presence of benzyltrimethylammonium hydroxide. An article, product, or composition comprising one or more compounds according to any one of claims 1-3. 11. The article, product, or composition of Claim 10, wherein said article, product, or composition further comprises a carrier solvent, water, alcohol, alkylene glycol, alkylene glycol alkyl ether, or combinations thereof. 12. The article, product, or composition of claim 11, wherein the carrier solvent is methanol, ethanol, propanol, isopropanol, butanol, isobutanol, monoethylene glycol, ethylene glycol monobutyl ether, or combinations thereof. The article, product, or composition further comprises a primary alkalinity source and is a detergent composition, wherein the primary alkalinity source is alkali metal hydroxide, alkali metal carbonate, alkali metal silicate, alkali metal metasilicate 13. The article, product, or composition of claims 11 or 12, which is a salt, alkanoamine, amine, or mixture thereof. 14. The article, product, or composition of claim 13, wherein said article, product, or composition further comprises a builder, an enzyme, a chelating agent, a surfactant, one or more additional detergent composition agents, or combinations thereof. Or composition. the enzyme is a protease enzyme,
The chelating agent is methylglycinediacetic acid (MGDA), glutamic acid-N,N-diacetic acid (GLDA), N-hydroxyethylaminodiacetic acid, ethylenediaminetetraacetic acid (EDTA), hydroxyethylenediaminetetraacetic acid, diethylenetriaminepentaacetic acid, N -hydroxyethyl-ethylenediaminetriacetic acid (HEDTA), diethylenetriaminepentaacetic acid (DTPA), ethylenediaminesuccinic acid (EDDS), 2-hydroxyethyliminodiacetic acid (HEIDA), iminodisuccinic acid (IDS), 3-hydroxy-2-2' - is iminodisuccinic acid (HIDS), or a mixture thereof, and/or
15. The article, product of claim 14, wherein said surfactant is a nonionic, semi-nonionic, cationic, anionic, amphoteric, zwitterionic, gemini surfactant, or mixtures thereof. Or composition. 16. The article, product, or composition of claims 14 or 15, wherein said composition is a solid, multi-use solid, or multi-use pressed solid composition. A method for inhibiting corrosion on a surface in an aqueous system comprising:
providing a corrosion control composition or a use solution of said corrosion control composition into a water system to produce a treated water system or on a surface of said water system;
said corrosion control composition comprises a compound according to Formula I, optionally one or more compounds according to one of Formula II, Formula III, and one or more additional corrosion control composition agents;

During the ceremony,
X is NH;
R ¹¹ is a C ₆ -C ₂₀ alkenyl group having at least one trans or cis double bond;
^R2 is H or _CH3 ;
R ³ is CH ₂ , CH ₂ CH ₂ , or C(CH ₃ ) ₂ ;
Y is —NR ⁴ R ⁵ R ⁶⁽⁺⁾ , or a salt thereof;
R ⁴ and R ⁵ are independently CH ₃ and R ⁶ is CH ₃ , C ₂ -C ₁₂ aromatic alkyl, or —CH ₂ —C ₆ H ₅ ;
Y′ is —COOH, —SO ₃ H, —PO ₃ H, —OSO ₃ H, —OPO ₃ H, or a salt thereof;
R ² ' is H, CH ₃ , or an unsubstituted or substituted straight or branched chain C ₁ -C ₁₀ alkyl, alkenyl, alkynyl group, —COOH, —CH ₂ COOH, Y', or —(CH ₂ ) _m -Y',
The method, wherein the corrosion control composition mitigates corrosion on the surface in the aqueous system. 18. The method of claim 17, wherein Y is -NR ⁴ R ⁵ R ⁶⁽⁺⁾ , or N(CH ₃ ) ₃ ⁺ . The corrosion control composition comprises water, an organic solvent, one or more additional corrosion inhibitors, surfactants, scale inhibitors, gas hydrate inhibitors, pH adjusters, emulsion breakers, inverse emulsion breakers, Fouling control agents, coagulants/flocculants, emulsifiers, water purification agents, dispersants, antioxidants, polymeric antidegradants, permeability modifiers, blowing agents, defoamers, emulsifying agents, CO ₂ and/or O ₂ scavengers, gelling agents, lubricants, friction modifiers, salts, or mixtures thereof. The corrosion control composition agent is a biocide, and the biocide is chlorine, hypochlorite, _ClO2 , bromide, ozone, hydrogen peroxide, peracetic acid, peroxysulfuric acid, peroxycarboxylic acid composition. , glutaraldehyde, dibromonitrilopropionamide, isothiazolone, terbuthylazine, polymeric biguanide, methylenebisthiocyanate, tetrakishydroxymethylphosphonium sulfate, or any combination thereof. . wherein said corrosion control composition agent is an acid, said corrosion control composition comprises from about 1% to about 20% by weight of said acid, said acid being hydrochloric acid, hydrofluoric acid, citric acid, formic acid, The method according to any one of claims 17-18, which is acetic acid, or a mixture thereof. The corrosion control composition of claims 17-21, wherein the corrosion control composition is a liquid, a gel, or a mixture comprising a liquid/gel and a solid, and wherein the corrosion control composition or its use solution has a pH of about 1 to about 11. A method according to any one of paragraphs. 23. The corrosion control composition of any one of claims 17-22, wherein the corrosion control composition comprises from about 10% to about 80% by weight of the composition and has a concentration in the treated water system of from about 1 ppm to about 1000 ppm. The method described in section. Said water systems include cooling water systems, boiler water systems, water systems in oil and gas operations, oil wells, downhole formation, geothermal wells, mineral washing, flotation and charities, papermaking, gas scrubbers, air washers, continuous casting processes in the metallurgical industry, air conditioning. and refrigeration, water recycling, water purification, membrane filtration, food processing, clarifiers, municipal sewage treatment, municipal water treatment, or drinking water systems, wherein said water systems are fresh water, process water, salt water, surface water, produced water, The method of any one of claims 17-23, comprising oils, hydrocarbons, solids, or mixtures thereof. A corrosion control composition comprising a compound according to Formula I, optionally one or more compounds according to one of Formula II, Formula III, and one or more additional corrosion control composition agents,

During the ceremony,
X is NH;
R ¹¹ is a C ₆ -C ₂₀ alkenyl group having at least one trans or cis double bond;
^R2 is H or _CH3 ;
R ³ is CH ₂ , CH ₂ CH ₂ , or C(CH ₃ ) ₂ ;
Y is —NR ⁴ R ⁵ R ⁶⁽⁺⁾ , or a salt thereof;
R ⁴ and R ⁵ are independently CH ₃ and R ⁶ is CH ₃ , C ₂ -C ₁₂ aromatic alkyl, or —CH ₂ —C ₆ H ₅ ;
Y′ is —COOH, —SO ₃ H, —PO ₃ H, —OSO ₃ H, —OPO ₃ H, or a salt thereof;
R ² ' is H, CH ₃ , or an unsubstituted or substituted straight or branched chain C ₁ -C ₁₀ alkyl, alkenyl, alkynyl group, —COOH, —CH ₂ COOH, Y', or —(CH ₂ ) _m -Y',
A corrosion control composition, wherein the corrosion control composition mitigates surface corrosion in aqueous systems.

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